The Importance of 1,5-Oxygen center dot center dot Chalcogen Interactions in Enantioselective Isochalcogenourea Catalysis

The importance of 1,5-O center dot center dot center dot chalcogen (Ch) interactions in isochalcogenourea catalysis (Ch=O, S, Se) is investigated. Conformational analyses of N-acyl isochalcogenouronium species and comparison with kinetic data demonstrate the significance of 1,5-O center dot center d...

Full description

Saved in:
Bibliographic Details
Published inAngewandte Chemie International Edition Vol. 59; no. 9; pp. 3705 - 3710
Main Authors Young, Claire M., Elmi, Alex, Pascoe, Dominic J., Morris, Rylie K., McLaughlin, Calum, Woods, Andrew M., Frost, Aileen B., de la Houpliere, Alix, Ling, Kenneth B., Smith, Terry K., Slawin, Alexandra M. Z., Willoughby, Patrick H., Cockroft, Scott L., Smith, Andrew D.
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 24.02.2020
Subjects
Online AccessGet full text

Cover

Loading…
Abstract The importance of 1,5-O center dot center dot center dot chalcogen (Ch) interactions in isochalcogenourea catalysis (Ch=O, S, Se) is investigated. Conformational analyses of N-acyl isochalcogenouronium species and comparison with kinetic data demonstrate the significance of 1,5-O center dot center dot center dot Ch interactions in enantioselective catalysis. Importantly, the selenium analogue demonstrates enhanced rate and selectivity profiles across a range of reaction processes including nitronate conjugate addition and formal [4+2] cycloadditions. A gram-scale synthesis of the most active selenium analogue was developed using a previously unreported seleno-Hugerschoff reaction, allowing the challenging kinetic resolutions of tertiary alcohols to be performed at 500 ppm catalyst loading. Density functional theory (DFT) and natural bond orbital (NBO) calculations support the role of orbital delocalization (occurring by intramolecular chalcogen bonding) in determining the conformation, equilibrium population, and reactivity of N-acylated intermediates.
AbstractList The importance of 1,5-O center dot center dot center dot chalcogen (Ch) interactions in isochalcogenourea catalysis (Ch=O, S, Se) is investigated. Conformational analyses of N-acyl isochalcogenouronium species and comparison with kinetic data demonstrate the significance of 1,5-O center dot center dot center dot Ch interactions in enantioselective catalysis. Importantly, the selenium analogue demonstrates enhanced rate and selectivity profiles across a range of reaction processes including nitronate conjugate addition and formal [4+2] cycloadditions. A gram-scale synthesis of the most active selenium analogue was developed using a previously unreported seleno-Hugerschoff reaction, allowing the challenging kinetic resolutions of tertiary alcohols to be performed at 500 ppm catalyst loading. Density functional theory (DFT) and natural bond orbital (NBO) calculations support the role of orbital delocalization (occurring by intramolecular chalcogen bonding) in determining the conformation, equilibrium population, and reactivity of N-acylated intermediates.
Author Elmi, Alex
McLaughlin, Calum
de la Houpliere, Alix
Willoughby, Patrick H.
Woods, Andrew M.
Young, Claire M.
Smith, Terry K.
Smith, Andrew D.
Pascoe, Dominic J.
Ling, Kenneth B.
Morris, Rylie K.
Frost, Aileen B.
Slawin, Alexandra M. Z.
Cockroft, Scott L.
Author_xml – sequence: 1
  givenname: Claire M.
  orcidid: 0000-0002-2923-4228
  surname: Young
  fullname: Young, Claire M.
  organization: Univ St Andrews, EaStCHEM Sch Chem, St Andrews KY16 9ST, Fife, Scotland
– sequence: 2
  givenname: Alex
  surname: Elmi
  fullname: Elmi, Alex
  organization: Univ Edinburgh, EaStCHEM Sch Chem, Joseph Black Bldg,David Brewster Rd, Edinburgh EH9 3FJ, Midlothian, Scotland
– sequence: 3
  givenname: Dominic J.
  surname: Pascoe
  fullname: Pascoe, Dominic J.
  organization: Univ Edinburgh, EaStCHEM Sch Chem, Joseph Black Bldg,David Brewster Rd, Edinburgh EH9 3FJ, Midlothian, Scotland
– sequence: 4
  givenname: Rylie K.
  orcidid: 0000-0001-5305-6006
  surname: Morris
  fullname: Morris, Rylie K.
  organization: Ripon Coll, Chem Dept, 300 W Seward St, Ripon, WI 54971 USA
– sequence: 5
  givenname: Calum
  surname: McLaughlin
  fullname: McLaughlin, Calum
  organization: Univ St Andrews, EaStCHEM Sch Chem, St Andrews KY16 9ST, Fife, Scotland
– sequence: 6
  givenname: Andrew M.
  surname: Woods
  fullname: Woods, Andrew M.
  organization: Univ St Andrews, EaStCHEM Sch Chem, St Andrews KY16 9ST, Fife, Scotland
– sequence: 7
  givenname: Aileen B.
  surname: Frost
  fullname: Frost, Aileen B.
  organization: Univ St Andrews, EaStCHEM Sch Chem, St Andrews KY16 9ST, Fife, Scotland
– sequence: 8
  givenname: Alix
  surname: de la Houpliere
  fullname: de la Houpliere, Alix
  organization: Univ St Andrews, EaStCHEM Sch Chem, St Andrews KY16 9ST, Fife, Scotland
– sequence: 9
  givenname: Kenneth B.
  surname: Ling
  fullname: Ling, Kenneth B.
  organization: Syngenta, Jealotts Hill Int Res Ctr, Bracknell RG42 6EY, Berks, England
– sequence: 10
  givenname: Terry K.
  surname: Smith
  fullname: Smith, Terry K.
  organization: Univ St Andrews, EaStCHEM Sch Chem, St Andrews KY16 9ST, Fife, Scotland
– sequence: 11
  givenname: Alexandra M. Z.
  orcidid: 0000-0002-9527-6418
  surname: Slawin
  fullname: Slawin, Alexandra M. Z.
  organization: Univ St Andrews, EaStCHEM Sch Chem, St Andrews KY16 9ST, Fife, Scotland
– sequence: 12
  givenname: Patrick H.
  orcidid: 0000-0001-5163-0502
  surname: Willoughby
  fullname: Willoughby, Patrick H.
  email: willoughbyp@ripon.edu
  organization: Ripon Coll, Chem Dept, 300 W Seward St, Ripon, WI 54971 USA
– sequence: 13
  givenname: Scott L.
  orcidid: 0000-0001-9321-8997
  surname: Cockroft
  fullname: Cockroft, Scott L.
  email: scott.cockroft@ed.ac.uk
  organization: Univ Edinburgh, EaStCHEM Sch Chem, Joseph Black Bldg,David Brewster Rd, Edinburgh EH9 3FJ, Midlothian, Scotland
– sequence: 14
  givenname: Andrew D.
  orcidid: 0000-0002-2104-7313
  surname: Smith
  fullname: Smith, Andrew D.
  email: ads10@st-andrews.ac.uk
  organization: Univ St Andrews, EaStCHEM Sch Chem, St Andrews KY16 9ST, Fife, Scotland
BookMark eNqVjr1PwzAQxS3Uin7AyuwdUnxx3KRzVNROLN2rq7lQo_RcxS6Q_x5HAokRpvvdu6d7byZG7JmEuAO1AKXyR2RHi1zBCooihysxBZNDpstSjxIXWmdlZWAiZiG8JX9VqeW1mGiozFKXeir63ZHk9nT2XUS2JH0j4cFkz5_9K7G0xJE6-eLjb6yP2Fo_3LeDhjY6z0E6lmtGTkuglpL4nj4Hb3_c_tIRyhojtn1w4UaMG2wD3X7Pubh_Wu_qTfZBB98E6yj12Z87d8Ku3yulDKhiVZpECvRcVH931y7i0LH2F476f0FfPUpu5w
Cites_doi 10.1002/anie.201600547
10.1038/s41557-018-0065-0
10.1021/jm501853m
10.1021/ol060065s
10.1039/c6sc00940a
10.1039/c2cs35213c
10.1039/c1cs15206h
10.1039/c4sc01746c
10.1002/chem.201604788
10.1021/ja9086352
10.1039/c3sc50199j
10.1039/b822665m
10.1016/j.tetlet.2006.04.109
10.1039/c8cp06908e
10.1002/anie.201706402
10.1039/b704781a
10.1016/j.tet.2018.05.069
10.1002/anie.201910639
10.1021/jo0349431
10.1002/chem.201704502
10.1515/pac-2018-0713
10.1021/jacs.5b13006
10.1021/ja016348r
10.1021/jacs.6b01462
10.1002/ejoc.201600399
10.1021/ol0623419
10.1002/anie.201809432
10.1039/c7fd00199a
10.1021/cr900352j
10.1002/anie.201712456
10.1021/ja501005g
10.1021/cr068373r
10.1021/jacs.7b08511
10.1351/PAC-REC-12-05-10
10.1021/ja049690n
10.1021/jacs.6b11851
10.1002/anie.201801452
10.1021/ol071223y
10.1039/c3sc51791h
10.1002/anie.201611019
10.1002/anie.201704816
ContentType Journal Article
DBID 1KM
AOWDO
BLEPL
DTL
DOI 10.1002/anie.201914421
DatabaseName Index Chemicus
Web of Science - Science Citation Index Expanded - 2020
Web of Science Core Collection
Science Citation Index Expanded
DatabaseTitle Web of Science
DatabaseTitleList Web of Science
Database_xml – sequence: 1
  dbid: 1KM
  name: Index Chemicus
  url: https://proxy.k.utb.cz/login?url=https://www.webofscience.com/wos/woscc/search-with-editions?editions=WOS.IC
  sourceTypes:
    Index Database
    Enrichment Source
DeliveryMethod fulltext_linktorsrc
Discipline Chemistry
EISSN 1521-3773
EndPage 3710
ExternalDocumentID 000510497500001
GrantInformation_xml – fundername: American Chemical Society Petroleum Research Fund; American Chemical Society
– fundername: Syngenta
– fundername: EPSRC; UK Research & Innovation (UKRI); Engineering & Physical Sciences Research Council (EPSRC)
  grantid: 1792153
– fundername: National Science Foundation; National Science Foundation (NSF)
  grantid: NSF-MRI: CHE-1429616
– fundername: Philip Leverhulme Prize; Leverhulme Trust
GroupedDBID ---
-DZ
-~X
.3N
.GA
05W
0R~
10A
1KM
1L6
1OB
1OC
1ZS
23M
33P
3SF
3WU
4.4
4ZD
50Y
50Z
51W
51X
52M
52N
52O
52P
52S
52T
52U
52W
52X
53G
5GY
5RE
5VS
66C
6TJ
702
7PT
8-0
8-1
8-3
8-4
8-5
8UM
930
A03
AAESR
AAEVG
AAHHS
AAMNL
AANLZ
AAONW
AASGY
AAXRX
AAZKR
ABCQN
ABCUV
ABEML
ABIJN
ABLJU
ABPPZ
ABPVW
ACAHQ
ACCFJ
ACCZN
ACFBH
ACGFS
ACIWK
ACNCT
ACPOU
ACPRK
ACSCC
ACXBN
ACXQS
ADBBV
ADEOM
ADIZJ
ADKYN
ADMGS
ADOZA
ADXAS
ADZMN
ADZOD
AEEZP
AEIGN
AEIMD
AEQDE
AEUQT
AEUYR
AFBPY
AFFNX
AFFPM
AFGKR
AFPWT
AFRAH
AFZJQ
AHBTC
AHMBA
AITYG
AIURR
AIWBW
AJBDE
AJXKR
ALAGY
ALMA_UNASSIGNED_HOLDINGS
ALUQN
AMBMR
AMYDB
ATUGU
AUFTA
AZBYB
AZVAB
B-7
BAFTC
BDRZF
BFHJK
BHBCM
BLEPL
BMNLL
BMXJE
BNHUX
BROTX
BRXPI
BTSUX
BY8
CS3
D-E
D-F
D0L
DCZOG
DPXWK
DR1
DR2
DRFUL
DRSTM
DTL
EBS
F00
F01
F04
F5P
G-S
G.N
GNP
GODZA
GROUPED_WOS_WEB_OF_SCIENCE
H.T
H.X
HBH
HGLYW
HHY
HHZ
HZ~
IX1
J0M
JPC
KQQ
LATKE
LAW
LC2
LC3
LEEKS
LH4
LITHE
LOXES
LP6
LP7
LUTES
LYRES
M53
MEWTI
MK4
MRFUL
MRSTM
MSFUL
MSSTM
MXFUL
MXSTM
N04
N05
N9A
NF~
NNB
O66
O9-
OIG
P2P
P2W
P2X
P4D
PQQKQ
Q.N
Q11
QB0
QRW
R.K
RNS
ROL
RWI
RX1
RYL
SUPJJ
TN5
UB1
UPT
UQL
V2E
VQA
W8V
W99
WBFHL
WBKPD
WH7
WIB
WIH
WIK
WJL
WOHZO
WQJ
WRC
WXSBR
WYISQ
XG1
XPP
XSW
XV2
YZZ
ZZTAW
~IA
~KM
~WT
ID FETCH-webofscience_primary_0005104975000013
ISICitedReferencesCount 105
ISICitedReferencesURI https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=CitingArticles&UT=000510497500001
ISSN 1433-7851
IngestDate Fri Dec 13 17:31:08 EST 2024
Sat Nov 23 06:42:17 EST 2024
IsPeerReviewed true
IsScholarly true
Issue 9
Keywords organocatalysis
DEFINITION
THERMODYNAMICS
ASYMMETRIC METHOXYSELENENYLATION
isothioureas
isoselenoureas
SULFUR
DISELENIDE
asymmetric catalysis
chalcogen bonding
ELECTROPHILES
SALTS
Language English
LinkModel OpenURL
LogoURL https://exlibris-pub.s3.amazonaws.com/fromwos-v2.jpg
MergedId FETCHMERGED-webofscience_primary_0005104975000013
Notes UKRI
ORCID 0000-0001-5305-6006
0000-0001-9321-8997
0000-0002-9527-6418
0000-0002-2923-4228
0000-0002-2104-7313
0000-0001-5163-0502
PMID 31856373
PageCount 6
ParticipantIDs webofscience_primary_000510497500001CitationCount
webofscience_primary_000510497500001
PublicationCentury 2000
PublicationDate 2020-02-24
PublicationDateYYYYMMDD 2020-02-24
PublicationDate_xml – month: 02
  year: 2020
  text: 2020-02-24
  day: 24
PublicationDecade 2020
PublicationPlace WEINHEIM
PublicationPlace_xml – name: WEINHEIM
PublicationTitle Angewandte Chemie International Edition
PublicationTitleAbbrev ANGEW CHEM INT EDIT
PublicationYear 2020
Publisher Wiley
Publisher_xml – name: Wiley
References Matviitsuk, A. (000510497500001.40) 2017; 129
Merad, J (WOS:000390760000001) 2016; 2016
Tiecco, M (WOS:000174265200014) 2002; 8
Iwaoka, M (WOS:000220957900061) 2004; 126
Beale, TM (WOS:000314179200013) 2013; 42
Browne, DM (WOS:000248315900053) 2007; 9
ROSENFIELD, RE (WOS:A1977DL95500072) 1977; 99
Matviitsuk, A (WOS:000411267800044) 2017; 56
Kennedy, CR (WOS:000385713200004) 2016; 55
Benz, S. (000510497500001.9) 2018; 130
Zhao, YJ (WOS:000373748000001) 2016; 138
LAITINEN, R (WOS:A1986C869500006) 1986
Mukherjee, AJ (WOS:000280140400015) 2010; 110
WIRTH, T (WOS:A1995RU32500007) 1995; 34
Wirth, T. (000510497500001.57) 1995; 107
Hugershoff, A (WOS:000201156200086) 1903; 36
Iwaoka, M (WOS:000174191400025) 2002; 124
Giacalone, F (WOS:000300797700022) 2012; 41
Morrill, LC (WOS:000325409500007) 2013; 4
Hugershoff, A (WOS:000201155400275) 1901; 34
FUJITA, K (WOS:A1994NP40700028) 1994
Wirth, T (WOS:000072692400005) 1998; 9
Greenhalgh, M. D. (000510497500001.25) 2018; 130
Benz, S (WOS:000431035500039) 2018; 57
Robinson, ERT (WOS:000391453200006) 2016; 7
Birman, VB (WOS:000236397000025) 2006; 8
FUJITA, KI (WOS:A1995RQ54800020) 1995
Benz, S (WOS:000394996900024) 2017; 56
Bae, HY (WOS:000439420400016) 2018; 10
Vogel, L. (000510497500001.54) 2019; 131
Greenhalgh, MD (WOS:000426759900035) 2018; 57
West, TH (WOS:000398247100033) 2017; 139
Abbasov, ME (WOS:000333551800012) 2014; 136
Doyle, AG (WOS:000251583300009) 2007; 107
BURLING, FT (WOS:A1992HK67100004) 1992; 114
Robertson, CC (WOS:000343004300007) 2014; 5
Cerny, J (WOS:000249925500010) 2007; 9
Kagan, H. B. (000510497500001.31) 1988; 18
Jordan, AD (WOS:000186156700053) 2003; 68
Tiecco, M (WOS:000166664400005) 2000; 11
Birman, VB (WOS:000243124900010) 2007; 9
Brammer, L (WOS:000412816300023) 2017; 203
Kennedy, C. R. (000510497500001.34) 2016; 128
Wonner, P. (000510497500001.61) 2019; 131
Fukuzawa, S (WOS:A1997YD81100034) 1997; 62
Sarwar, MG (WOS:000275084900055) 2010; 132
Robinson, ERT (WOS:000316966500034) 2013; 4
Mati, IK (WOS:000283141300014) 2010; 39
Lehn, JM (WOS:000174712600040) 2002; 295
FUJITA, K (WOS:A1995RK63600030) 1995; 36
Kobayashi, M (WOS:000238407500007) 2006; 47
Aakeroy, CB (WOS:000496795300017) 2019; 91
Kawamata, Y (WOS:000375244700007) 2016; 138
Pascoe, DJ (WOS:000414115800051) 2017; 139
Vogel, L (WOS:000458828000003) 2019; 58
Montero-Campillo, MM (WOS:000461667900001) 2019; 21
Musolino, SF (WOS:000393219300039) 2016; 22
Wonner, P (WOS:000410810600064) 2017; 56
Benz, S. (000510497500001.6) 2017; 129
Desiraju, GR (WOS:000322624300011) 2013; 85
Beno, BR (WOS:000356316600002) 2015; 58
Wonner, P (WOS:000494188400001) 2019; 58
Wonner, P (WOS:000418570000010) 2017; 23
Wonner, P. (000510497500001.62) 2017; 129
Greenhalgh, MD (WOS:000445305400073) 2018; 74
References_xml – volume: 34
  start-page: 1726
  year: 1995
  ident: WOS:A1995RU32500007
  article-title: ASYMMETRIC REACTION OF ARYLALKENES WITH DISELENIDES
  publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH
  contributor:
    fullname: WIRTH, T
– volume: 9
  start-page: 547
  year: 1998
  ident: WOS:000072692400005
  article-title: Catalytic asymmetric oxyselenenylation-elimination reactions using chiral selenium compounds
  publication-title: TETRAHEDRON-ASYMMETRY
  contributor:
    fullname: Wirth, T
– volume: 114
  start-page: 2313
  year: 1992
  ident: WOS:A1992HK67100004
  article-title: COMPUTATIONAL STUDIES OF NONBONDED SULFUR OXYGEN AND SELENIUM OXYGEN INTERACTIONS IN THE THIAZOLE AND SELENAZOLE NUCLEOSIDES
  publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  contributor:
    fullname: BURLING, FT
– volume: 131
  start-page: 17079
  year: 2019
  ident: 000510497500001.61
  publication-title: Angew. Chem.
  contributor:
    fullname: Wonner, P.
– volume: 55
  start-page: 12596
  year: 2016
  ident: WOS:000385713200004
  article-title: The Cation-pi Interaction in Small-Molecule Catalysis
  publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
  doi: 10.1002/anie.201600547
  contributor:
    fullname: Kennedy, CR
– start-page: 1641
  year: 1995
  ident: WOS:A1995RQ54800020
  article-title: ASYMMETRIC INTRAMOLECULAR SELENOETHERIFICATION AND SELENOLACTONIZATION USING AN OPTICALLY-ACTIVE DIARYL DISELENIDE DERIVED FROM D-MANNITOL
  publication-title: JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS
  contributor:
    fullname: FUJITA, KI
– volume: 10
  start-page: 888
  year: 2018
  ident: WOS:000439420400016
  article-title: Approaching sub-ppm-level asymmetric organocatalysis of a highly challenging and scalable carbon-carbon bond forming reaction
  publication-title: NATURE CHEMISTRY
  doi: 10.1038/s41557-018-0065-0
  contributor:
    fullname: Bae, HY
– volume: 18
  start-page: 249
  year: 1988
  ident: 000510497500001.31
  article-title: Kinetic Resolution
  publication-title: Topics in Stereochemistry
  contributor:
    fullname: Kagan, H. B.
– volume: 58
  start-page: 4383
  year: 2015
  ident: WOS:000356316600002
  article-title: A Survey of the Role of Noncovalent Sulfur Interactions in Drug Design
  publication-title: JOURNAL OF MEDICINAL CHEMISTRY
  doi: 10.1021/jm501853m
  contributor:
    fullname: Beno, BR
– volume: 8
  start-page: 1351
  year: 2006
  ident: WOS:000236397000025
  article-title: Benzotetramisole: A remarkably enantioselective acyl transfer catalyst
  publication-title: ORGANIC LETTERS
  doi: 10.1021/ol060065s
  contributor:
    fullname: Birman, VB
– volume: 7
  start-page: 6919
  year: 2016
  ident: WOS:000391453200006
  article-title: Non-bonding 1,5-S center dot center dot center dot O interactions govern chemo- and enantioselectivity in isothiourea-catalyzed annulations of benzazoles
  publication-title: CHEMICAL SCIENCE
  doi: 10.1039/c6sc00940a
  contributor:
    fullname: Robinson, ERT
– volume: 129
  start-page: 12172
  year: 2017
  ident: 000510497500001.62
  publication-title: Angew. Chem.
  contributor:
    fullname: Wonner, P.
– volume: 42
  start-page: 1667
  year: 2013
  ident: WOS:000314179200013
  article-title: Halogen bonding in solution: thermodynamics and applications
  publication-title: CHEMICAL SOCIETY REVIEWS
  doi: 10.1039/c2cs35213c
  contributor:
    fullname: Beale, TM
– volume: 99
  start-page: 4860
  year: 1977
  ident: WOS:A1977DL95500072
  article-title: DIRECTIONAL PREFERENCES OF NONBONDED ATOMIC CONTACTS WITH DIVALENT SULFUR .1. ELECTROPHILES AND NUCLEOPHILES
  publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  contributor:
    fullname: ROSENFIELD, RE
– volume: 41
  start-page: 2406
  year: 2012
  ident: WOS:000300797700022
  article-title: Low-loading asymmetric organocatalysis
  publication-title: CHEMICAL SOCIETY REVIEWS
  doi: 10.1039/c1cs15206h
  contributor:
    fullname: Giacalone, F
– volume: 5
  start-page: 4179
  year: 2014
  ident: WOS:000343004300007
  article-title: A solvent-resistant halogen bond
  publication-title: CHEMICAL SCIENCE
  doi: 10.1039/c4sc01746c
  contributor:
    fullname: Robertson, CC
– volume: 36
  start-page: 3121
  year: 1903
  ident: WOS:000201156200086
  article-title: The effect of bromine on aromatic thio urea
  publication-title: BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT
  contributor:
    fullname: Hugershoff, A
– volume: 129
  start-page: 12450
  year: 2017
  ident: 000510497500001.40
  publication-title: Angew. Chem.
  contributor:
    fullname: Matviitsuk, A.
– volume: 22
  start-page: 18916
  year: 2016
  ident: WOS:000393219300039
  article-title: Isothiourea-Catalysed Acylative Kinetic Resolution of Aryl-Alkenyl (sp(2) vs. sp(2)) Substituted Secondary Alcohols
  publication-title: CHEMISTRY-A EUROPEAN JOURNAL
  doi: 10.1002/chem.201604788
  contributor:
    fullname: Musolino, SF
– volume: 132
  start-page: 1646
  year: 2010
  ident: WOS:000275084900055
  article-title: Thermodynamics of Halogen Bonding in Solution: Substituent, Structural, and Solvent Effects
  publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  doi: 10.1021/ja9086352
  contributor:
    fullname: Sarwar, MG
– volume: 4
  start-page: 2193
  year: 2013
  ident: WOS:000316966500034
  article-title: Anhydrides as alpha,beta-unsaturated acyl ammonium precursors: isothiourea-promoted catalytic asymmetric annulation processes
  publication-title: CHEMICAL SCIENCE
  doi: 10.1039/c3sc50199j
  contributor:
    fullname: Robinson, ERT
– volume: 39
  start-page: 4195
  year: 2010
  ident: WOS:000283141300014
  article-title: Molecular balances for quantifying non-covalent interactions
  publication-title: CHEMICAL SOCIETY REVIEWS
  doi: 10.1039/b822665m
  contributor:
    fullname: Mati, IK
– volume: 47
  start-page: 4347
  year: 2006
  ident: WOS:000238407500007
  article-title: Unexpected reactivity of annulated 3H-benzothiazol-2-ylideneamines as an acyl transfer catalyst
  publication-title: TETRAHEDRON LETTERS
  doi: 10.1016/j.tetlet.2006.04.109
  contributor:
    fullname: Kobayashi, M
– volume: 21
  start-page: 2222
  year: 2019
  ident: WOS:000461667900001
  article-title: Modulating the intrinsic reactivity of molecules through non-covalent interactions
  publication-title: PHYSICAL CHEMISTRY CHEMICAL PHYSICS
  doi: 10.1039/c8cp06908e
  contributor:
    fullname: Montero-Campillo, MM
– volume: 56
  start-page: 12282
  year: 2017
  ident: WOS:000411267800044
  article-title: Aryloxide-Facilitated Catalyst Turnover in Enantioselective ,-Unsaturated Acyl Ammonium Catalysis
  publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
  doi: 10.1002/anie.201706402
  contributor:
    fullname: Matviitsuk, A
– volume: 9
  start-page: 5291
  year: 2007
  ident: WOS:000249925500010
  article-title: Non-covalent interactions in biomacromolecules
  publication-title: PHYSICAL CHEMISTRY CHEMICAL PHYSICS
  doi: 10.1039/b704781a
  contributor:
    fullname: Cerny, J
– volume: 74
  start-page: 5554
  year: 2018
  ident: WOS:000445305400073
  article-title: Best practice considerations for using the selectivity factor, s, as a metric for the efficiency of kinetic resolutions
  publication-title: TETRAHEDRON
  doi: 10.1016/j.tet.2018.05.069
  contributor:
    fullname: Greenhalgh, MD
– volume: 130
  start-page: 3254
  year: 2018
  ident: 000510497500001.25
  publication-title: Angew. Chem.
  contributor:
    fullname: Greenhalgh, M. D.
– volume: 58
  start-page: 16923
  year: 2019
  ident: WOS:000494188400001
  article-title: Chalcogen Bonding Catalysis of a Nitro-Michael Reaction
  publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
  doi: 10.1002/anie.201910639
  contributor:
    fullname: Wonner, P
– volume: 68
  start-page: 8693
  year: 2003
  ident: WOS:000186156700053
  article-title: Efficient conversion of substituted aryl thioureas to 2-aminobenzothiazoles using benzyltrimethylammonium tribromide
  publication-title: JOURNAL OF ORGANIC CHEMISTRY
  doi: 10.1021/jo0349431
  contributor:
    fullname: Jordan, AD
– volume: 23
  start-page: 16972
  year: 2017
  ident: WOS:000418570000010
  article-title: Catalytic Carbon-Chlorine Bond Activation by Selenium-Based Chalcogen Bond Donors
  publication-title: CHEMISTRY-A EUROPEAN JOURNAL
  doi: 10.1002/chem.201704502
  contributor:
    fullname: Wonner, P
– volume: 91
  start-page: 1889
  year: 2019
  ident: WOS:000496795300017
  article-title: Definition of the chalcogen bond (IUPAC Recommendations 2019)
  publication-title: PURE AND APPLIED CHEMISTRY
  doi: 10.1515/pac-2018-0713
  contributor:
    fullname: Aakeroy, CB
– volume: 138
  start-page: 4270
  year: 2016
  ident: WOS:000373748000001
  article-title: Unorthodox Interactions at Work
  publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  doi: 10.1021/jacs.5b13006
  contributor:
    fullname: Zhao, YJ
– volume: 124
  start-page: 1902
  year: 2002
  ident: WOS:000174191400025
  article-title: Quantitative evaluation of weak nonbonded Se center dot center dot center dot F interactions and their remarkable nature as orbital interactions
  publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  doi: 10.1021/ja016348r
  contributor:
    fullname: Iwaoka, M
– volume: 138
  start-page: 5206
  year: 2016
  ident: WOS:000375244700007
  article-title: A Chiral Electrophilic Selenium Catalyst for Highly Enantioselective Oxidative Cyclization
  publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  doi: 10.1021/jacs.6b01462
  contributor:
    fullname: Kawamata, Y
– volume: 62
  start-page: 7711
  year: 1997
  ident: WOS:A1997YD81100034
  article-title: Asymmetric methoxyselenenylation of alkenes with chiral ferrocenylselenium reagents
  publication-title: JOURNAL OF ORGANIC CHEMISTRY
  contributor:
    fullname: Fukuzawa, S
– volume: 2016
  start-page: 5589
  year: 2016
  ident: WOS:000390760000001
  article-title: Enantioselective Catalysis by Chiral Isothioureas
  publication-title: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
  doi: 10.1002/ejoc.201600399
  contributor:
    fullname: Merad, J
– volume: 9
  start-page: 37
  year: 2007
  ident: WOS:000243124900010
  article-title: Nonaromatic amidine derivatives as acylation catalysts
  publication-title: ORGANIC LETTERS
  doi: 10.1021/ol0623419
  contributor:
    fullname: Birman, VB
– volume: 107
  start-page: 1872
  year: 1995
  ident: 000510497500001.57
  publication-title: Angew. Chem.
  contributor:
    fullname: Wirth, T.
– volume: 58
  start-page: 1880
  year: 2019
  ident: WOS:000458828000003
  article-title: Chalcogen Bonding: An Overview
  publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
  doi: 10.1002/anie.201809432
  contributor:
    fullname: Vogel, L
– volume: 129
  start-page: 830
  year: 2017
  ident: 000510497500001.6
  article-title: Catalysis with Chalcogen Bonds
  publication-title: Angew. Chem.
  contributor:
    fullname: Benz, S.
– start-page: 1095
  year: 1986
  ident: WOS:A1986C869500006
  article-title: THE CRYSTAL-STRUCTURES OF THE HEXACHLOROANTIMONATE SALTS OF (CH3)2SS(CH3)+, (CH3S)3+, AND (CH3SE)3+
  publication-title: JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS
  contributor:
    fullname: LAITINEN, R
– volume: 203
  start-page: 485
  year: 2017
  ident: WOS:000412816300023
  article-title: Halogen bonding, chalcogen bonding, pnictogen bonding, tetrel bonding: origins, current status and discussion
  publication-title: FARADAY DISCUSSIONS
  doi: 10.1039/c7fd00199a
  contributor:
    fullname: Brammer, L
– volume: 110
  start-page: 4357
  year: 2010
  ident: WOS:000280140400015
  article-title: Organoselenium Chemistry: Role of Intramolecular Interactions
  publication-title: CHEMICAL REVIEWS
  doi: 10.1021/cr900352j
  contributor:
    fullname: Mukherjee, AJ
– volume: 57
  start-page: 3200
  year: 2018
  ident: WOS:000426759900035
  article-title: A C=O center dot center dot center dot Isothiouronium Interaction Dictates Enantiodiscrimination in Acylative Kinetic Resolutions of Tertiary Heterocyclic Alcohols
  publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
  doi: 10.1002/anie.201712456
  contributor:
    fullname: Greenhalgh, MD
– volume: 136
  start-page: 4492
  year: 2014
  ident: WOS:000333551800012
  article-title: Acylammonium Salts as Dienophiles in Diels-Alder/Lactonization Organocascades
  publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  doi: 10.1021/ja501005g
  contributor:
    fullname: Abbasov, ME
– volume: 107
  start-page: 5713
  year: 2007
  ident: WOS:000251583300009
  article-title: Small-molecule H-bond donors in asymmetric catalysis
  publication-title: CHEMICAL REVIEWS
  doi: 10.1021/cr068373r
  contributor:
    fullname: Doyle, AG
– volume: 295
  start-page: 2400
  year: 2002
  ident: WOS:000174712600040
  article-title: Toward self-organization and complex matter
  publication-title: SCIENCE
  contributor:
    fullname: Lehn, JM
– volume: 139
  start-page: 15160
  year: 2017
  ident: WOS:000414115800051
  article-title: The Origin of Chalcogen-Bonding Interactions
  publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  doi: 10.1021/jacs.7b08511
  contributor:
    fullname: Pascoe, DJ
– volume: 85
  start-page: 1711
  year: 2013
  ident: WOS:000322624300011
  article-title: Definition of the halogen bond (IUPAC Recommendations 2013)
  publication-title: PURE AND APPLIED CHEMISTRY
  doi: 10.1351/PAC-REC-12-05-10
  contributor:
    fullname: Desiraju, GR
– volume: 8
  start-page: 1118
  year: 2002
  ident: WOS:000174265200014
  article-title: Preparation of a new chiral non-racemic sulfur-containing diselenide and applications in asymmetric synthesis
  publication-title: CHEMISTRY-A EUROPEAN JOURNAL
  contributor:
    fullname: Tiecco, M
– start-page: 923
  year: 1994
  ident: WOS:A1994NP40700028
  article-title: SYNTHESIS OF DIARYL DISELENIDES HAVING CHIRAL PYRROLIDINE RINGS WITH C-2 SYMMETRY - THEIR APPLICATION TO THE ASYMMETRIC METHOXYSELENENYLATION OF TRANS-BETA-METHYLSTYRENES
  publication-title: CHEMISTRY LETTERS
  contributor:
    fullname: FUJITA, K
– volume: 126
  start-page: 5309
  year: 2004
  ident: WOS:000220957900061
  article-title: Nature of nonbonded Se center dot center dot center dot O interactions characterized by O-17 NMR spectroscopy and NBO and AIM analyses
  publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  doi: 10.1021/ja049690n
  contributor:
    fullname: Iwaoka, M
– volume: 139
  start-page: 4366
  year: 2017
  ident: WOS:000398247100033
  article-title: Catalytic Enantioselective [2,3]-Rearrangements of Allylic Ammonium Ylides: A Mechanistic and Computational Study
  publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  doi: 10.1021/jacs.6b11851
  contributor:
    fullname: West, TH
– volume: 57
  start-page: 5408
  year: 2018
  ident: WOS:000431035500039
  article-title: Catalysis with Pnictogen, Chalcogen, and Halogen Bonds
  publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
  doi: 10.1002/anie.201801452
  contributor:
    fullname: Benz, S
– volume: 9
  start-page: 3169
  year: 2007
  ident: WOS:000248315900053
  article-title: Catalytic use of selenium electrophiles in cyclizations
  publication-title: ORGANIC LETTERS
  doi: 10.1021/ol071223y
  contributor:
    fullname: Browne, DM
– volume: 130
  start-page: 5506
  year: 2018
  ident: 000510497500001.9
  publication-title: Angew. Chem.
  contributor:
    fullname: Benz, S.
– volume: 36
  start-page: 5219
  year: 1995
  ident: WOS:A1995RK63600030
  article-title: ASYMMETRIC METHOXYSELENENYLATION OF OLEFINS USING AN OPTICALLY-ACTIVE DIARYL DISELENIDE DERIVED FROM D-MANNITOL
  publication-title: TETRAHEDRON LETTERS
  contributor:
    fullname: FUJITA, K
– volume: 131
  start-page: 1896
  year: 2019
  ident: 000510497500001.54
  publication-title: Angew. Chem.
  contributor:
    fullname: Vogel, L.
– volume: 4
  start-page: 4146
  year: 2013
  ident: WOS:000325409500007
  article-title: Isothiourea-mediated asymmetric Michael-lactonisation of trifluoromethylenones: a synthetic and mechanistic study
  publication-title: CHEMICAL SCIENCE
  doi: 10.1039/c3sc51791h
  contributor:
    fullname: Morrill, LC
– volume: 34
  start-page: 3130
  year: 1901
  ident: WOS:000201155400275
  article-title: Effects of halogens on thiourea.
  publication-title: BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT
  contributor:
    fullname: Hugershoff, A
– volume: 128
  start-page: 12784
  year: 2016
  ident: 000510497500001.34
  publication-title: Angew. Chem.
  contributor:
    fullname: Kennedy, C. R.
– volume: 56
  start-page: 812
  year: 2017
  ident: WOS:000394996900024
  article-title: Catalysis with Chalcogen Bonds
  publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
  doi: 10.1002/anie.201611019
  contributor:
    fullname: Benz, S
– volume: 56
  start-page: 12009
  year: 2017
  ident: WOS:000410810600064
  article-title: Carbon-Halogen Bond Activation by Selenium-Based Chalcogen Bonding
  publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
  doi: 10.1002/anie.201704816
  contributor:
    fullname: Wonner, P
– volume: 11
  start-page: 4645
  year: 2000
  ident: WOS:000166664400005
  article-title: New nitrogen containing chiral diselenides: Synthesis and asymmetric addition reactions to olefins
  publication-title: TETRAHEDRON-ASYMMETRY
  contributor:
    fullname: Tiecco, M
SSID ssj0028806
Score 5.281357
Snippet The importance of 1,5-O center dot center dot center dot chalcogen (Ch) interactions in isochalcogenourea catalysis (Ch=O, S, Se) is investigated....
Source Web of Science
SourceID webofscience
SourceType Index Database
Enrichment Source
StartPage 3705
SubjectTerms Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
Title The Importance of 1,5-Oxygen center dot center dot Chalcogen Interactions in Enantioselective Isochalcogenourea Catalysis
URI http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000510497500001
Volume 59
WOS 000510497500001
WOSCitedRecordID wos000510497500001
hasFullText 1
inHoldings 1
isFullTextHit
isPrint
link http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV3JTsMwELUKSNALYhW7fOAWUtI4W48oFNEiQEIgcUPBdSBSm1QliOVz-RJm7CR1C4fCJbJS13U7r-NxPO8NIYcWc1gvsJkZBV5sOrHngh_s9UzOYTfBRcviUtTn8so7v3O69-59rfalZS295o8N_vkrr-Q_VoV7YFdkyf7BstWgcAPaYF-4goXhOrONOwMZQeP_E-I-8Euha16_f8B7DEy8xALgWa43w-eozzN8XT4NVMQGmRXbxqSYJHuRpXEwo6gDpit7Z5i-joRBJWKiB7Un6ZN4i5AXYEj9ATH1nLHdS_Tj_srBhP0owaICjXECySApWTfjs60XrtIVTzPUQeFGt-p_mY1GSiPh5gNiaeOioT_EgB0rksKdSVepeWGHMdMPCiVaUXhmuwneUNU9KV13ISauINrS_DDzLVdb05mvcmd_rBdKfxbJ_Jjl14LdpeJra-AZDiR6kGXuseLjJ2S7p5bTKslRhsewAfNdeYQyRxZQrBHrO5zeVBJnNvhPxYArvnIpLGrZx5PTqpPFcg6_BkkyILpdIcvFToaeKFiukppI18hSWBYQXCdYE5GO4UmzmDaPSnBShUgKiNSbFTipDk6apHQanPQHOGkFzg1inLVvw3NTn__DUAmrPEz9YmyTzKdZKrYItXyPY0AViThyHC9oxW7kMmH7fiAi2wm2yeEsI26T5izdwkIeH2Uh8p3Zht4l9TGw98h8PnoV-xCv5o8H0uDfhkeZBg
link.rule.ids 314,780,784,27924,27925
linkProvider Wiley-Blackwell
openUrl ctx_ver=Z39.88-2004&ctx_enc=info%3Aofi%2Fenc%3AUTF-8&rfr_id=info%3Asid%2Fsummon.serialssolutions.com&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=The+Importance+of+1%2C5-Oxygen+center+dot+center+dot+Chalcogen+Interactions+in+Enantioselective+Isochalcogenourea+Catalysis&rft.jtitle=Angewandte+Chemie+International+Edition&rft.au=Young%2C+Claire+M.&rft.au=Elmi%2C+Alex&rft.au=Pascoe%2C+Dominic+J.&rft.au=Morris%2C+Rylie+K.&rft.date=2020-02-24&rft.pub=Wiley&rft.issn=1433-7851&rft.eissn=1521-3773&rft.volume=59&rft.issue=9&rft.spage=3705&rft.epage=3710&rft_id=info:doi/10.1002%2Fanie.201914421&rft_id=info%3Apmid%2F31856373&rft.externalDBID=n%2Fa&rft.externalDocID=000510497500001
thumbnail_l http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=1433-7851&client=summon
thumbnail_m http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=1433-7851&client=summon
thumbnail_s http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=1433-7851&client=summon