Establishing the Reaction Pathways of the Catalytic Conversion of Erythrulose to Sulphides of Alpha‐Hydroxy Thioesters and Esters

Sulphides of alpha‐hydroxy thioesters and esters (SAH(T)Es) are important fine chemicals and have great potential as platform molecules. SAH(T)Es are typically synthesized from fossil sources while little is known regarding their synthesis from carbohydrates. We report our findings about the one‐pot...

Full description

Saved in:
Bibliographic Details
Published inChemCatChem Vol. 14; no. 8
Main Authors Calderon‐Ardila, Sergio, Matthijssen, Joost, Van Huffel, Bart, Péruch, Olivier, Morvan, Didier, Bellière‐Baca, Virginie, Dusselier, Michiel, Sels, Bert F.
Format Journal Article
LanguageEnglish
Published Weinheim Wiley Subscription Services, Inc 22.04.2022
Subjects
Online AccessGet full text

Cover

Loading…
Abstract Sulphides of alpha‐hydroxy thioesters and esters (SAH(T)Es) are important fine chemicals and have great potential as platform molecules. SAH(T)Es are typically synthesized from fossil sources while little is known regarding their synthesis from carbohydrates. We report our findings about the one‐pot chemocatalytic conversion of erythrulose (ERU) to SAH(T)Es. Sn, Mo and W chlorides were the most selective catalysts towards the synthesis of S‐butyl‐4‐butylthio‐2‐hydroxybutanethioate (BBTHBT) in 1‐BuSH. The selectivity towards BBTHBT was impacted by the formation of different thioacetals (TAs). The addition of either KOH, H2O or MeOH was effective to decrease TAs formation and increase selectivity towards BBTHBT (or its ester). A kinetic profile, in situ 13C NMR measurements and experiments at different temperatures complement our studies to unravel the complicated reaction network involved in the conversion of ERU to SAH(T)Es. This insight provides a solid foundation for future improvements in the sustainable synthesis of SAH(T)Es. We studied the Lewis acid catalyzed conversion of erythrulose to sulphides of alpha‐hydroxy thioesters and esters (SAH(T)Es). The addition of KOH, H2O or MeOH to the reaction mixture increased the selectivity towards SAH(T)Es by decreasing the thioacetalization side‐reactions. Our findings allowed to propose a reaction pathway that unravels the reaction network with placement of the most important intermediates and products of the reaction cascade.
AbstractList Abstract Sulphides of alpha‐hydroxy thioesters and esters (SAH(T)Es) are important fine chemicals and have great potential as platform molecules. SAH(T)Es are typically synthesized from fossil sources while little is known regarding their synthesis from carbohydrates. We report our findings about the one‐pot chemocatalytic conversion of erythrulose (ERU) to SAH(T)Es. Sn, Mo and W chlorides were the most selective catalysts towards the synthesis of S‐butyl‐4‐butylthio‐2‐hydroxybutanethioate (BBTHBT) in 1‐BuSH. The selectivity towards BBTHBT was impacted by the formation of different thioacetals (TAs). The addition of either KOH, H 2 O or MeOH was effective to decrease TAs formation and increase selectivity towards BBTHBT (or its ester). A kinetic profile, in situ 13 C NMR measurements and experiments at different temperatures complement our studies to unravel the complicated reaction network involved in the conversion of ERU to SAH(T)Es. This insight provides a solid foundation for future improvements in the sustainable synthesis of SAH(T)Es.
Sulphides of alpha‐hydroxy thioesters and esters (SAH(T)Es) are important fine chemicals and have great potential as platform molecules. SAH(T)Es are typically synthesized from fossil sources while little is known regarding their synthesis from carbohydrates. We report our findings about the one‐pot chemocatalytic conversion of erythrulose (ERU) to SAH(T)Es. Sn, Mo and W chlorides were the most selective catalysts towards the synthesis of S‐butyl‐4‐butylthio‐2‐hydroxybutanethioate (BBTHBT) in 1‐BuSH. The selectivity towards BBTHBT was impacted by the formation of different thioacetals (TAs). The addition of either KOH, H2O or MeOH was effective to decrease TAs formation and increase selectivity towards BBTHBT (or its ester). A kinetic profile, in situ 13C NMR measurements and experiments at different temperatures complement our studies to unravel the complicated reaction network involved in the conversion of ERU to SAH(T)Es. This insight provides a solid foundation for future improvements in the sustainable synthesis of SAH(T)Es. We studied the Lewis acid catalyzed conversion of erythrulose to sulphides of alpha‐hydroxy thioesters and esters (SAH(T)Es). The addition of KOH, H2O or MeOH to the reaction mixture increased the selectivity towards SAH(T)Es by decreasing the thioacetalization side‐reactions. Our findings allowed to propose a reaction pathway that unravels the reaction network with placement of the most important intermediates and products of the reaction cascade.
Sulphides of alpha‐hydroxy thioesters and esters (SAH(T)Es) are important fine chemicals and have great potential as platform molecules. SAH(T)Es are typically synthesized from fossil sources while little is known regarding their synthesis from carbohydrates. We report our findings about the one‐pot chemocatalytic conversion of erythrulose (ERU) to SAH(T)Es. Sn, Mo and W chlorides were the most selective catalysts towards the synthesis of S‐butyl‐4‐butylthio‐2‐hydroxybutanethioate (BBTHBT) in 1‐BuSH. The selectivity towards BBTHBT was impacted by the formation of different thioacetals (TAs). The addition of either KOH, H2O or MeOH was effective to decrease TAs formation and increase selectivity towards BBTHBT (or its ester). A kinetic profile, in situ 13C NMR measurements and experiments at different temperatures complement our studies to unravel the complicated reaction network involved in the conversion of ERU to SAH(T)Es. This insight provides a solid foundation for future improvements in the sustainable synthesis of SAH(T)Es.
Author Bellière‐Baca, Virginie
Matthijssen, Joost
Van Huffel, Bart
Calderon‐Ardila, Sergio
Sels, Bert F.
Péruch, Olivier
Dusselier, Michiel
Morvan, Didier
Author_xml – sequence: 1
  givenname: Sergio
  orcidid: 0000-0003-1760-6175
  surname: Calderon‐Ardila
  fullname: Calderon‐Ardila, Sergio
  organization: Katholieke Universiteit Leuven
– sequence: 2
  givenname: Joost
  orcidid: 0000-0003-3296-7139
  surname: Matthijssen
  fullname: Matthijssen, Joost
  organization: Katholieke Universiteit Leuven
– sequence: 3
  givenname: Bart
  surname: Van Huffel
  fullname: Van Huffel, Bart
  organization: Katholieke Universiteit Leuven
– sequence: 4
  givenname: Olivier
  surname: Péruch
  fullname: Péruch, Olivier
  organization: Adisseo France SAS
– sequence: 5
  givenname: Didier
  surname: Morvan
  fullname: Morvan, Didier
  organization: Adisseo France SAS
– sequence: 6
  givenname: Virginie
  surname: Bellière‐Baca
  fullname: Bellière‐Baca, Virginie
  organization: Adisseo France SAS
– sequence: 7
  givenname: Michiel
  orcidid: 0000-0002-3074-2318
  surname: Dusselier
  fullname: Dusselier, Michiel
  email: michiel.dusselier@kuleuven.be
  organization: Katholieke Universiteit Leuven
– sequence: 8
  givenname: Bert F.
  orcidid: 0000-0001-9657-1710
  surname: Sels
  fullname: Sels, Bert F.
  email: bert.sels@kuleuven.be
  organization: Katholieke Universiteit Leuven
BookMark eNqFkE1OwzAQhS1UJEphy9oS65Sx8-N4WUWBIlUCQVlHjuOQVCEutkPJDokLcEZOQtqismQ1TzPvmxm9UzRqdasQuiAwJQD0SkonpxQoAcJ8OEJjEkfM82PORwcdwwk6tXYFEHGfhWP0mVon8qa2Vd0-Y1cp_KCEdLVu8b1w1Ub0FutyN0iEE03vaokT3b4pY7emYZaa3lWma7RV2Gn82DXrqi7UjpsNWnx_fM37wuj3Hi-rWivrBhiLtsDpTp6h41I0Vp3_1gl6uk6Xydxb3N3cJrOFJ_2QgcdiyqjiZa44DSiTXEhQkWBxEQVlHkFIFOdBToY-YRD6UhY8zHMIeFkUpSD-BF3u966Nfu2GN7KV7kw7nMxoFPoQAqXh4JruXdJoa40qs7WpX4TpMwLZNuhsG3R2CHoA-B7Y1I3q_3FnSbJM_tgfPPuHMA
CitedBy_id crossref_primary_10_1039_D3GC03826B
Cites_doi 10.1002/cber.188501801187
10.1002/9780470171813.ch2
10.1002/chem.200305407
10.1021/cm402180t
10.1039/C6RA26708D
10.1007/s00253-014-6156-y
10.1021/cr60254a003
10.2172/15008859
10.1039/c0gc00923g
10.1073/pnas.1516466112
10.1039/c2gc16202d
10.1139/v75-125
10.1002/cssc.201400040
10.1021/ja00860a005
10.1021/ja01163a061
10.1021/ja01178a021
10.1039/C7GC02040F
10.1021/ja00486a048
10.1016/B978-0-12-802444-7.00011-2
10.1021/ja301678w
10.1021/acs.orglett.8b03986
10.1016/j.progpolymsci.2006.03.001
10.1016/j.ica.2015.04.011
10.1021/acscatal.5b01344
10.1002/cssc.201901742
10.1039/c3gc41492b
10.1055/s-2001-14912
10.1016/0021-9517(81)90272-4
10.1002/cssc.200900099
10.1039/C6GC01556E
10.1002/cctc.201200476
10.1002/cssc.201600757
10.1039/b501964h
10.1016/S0040-4039(98)00456-0
10.1126/science.1183990
10.1016/S0167-2991(07)80981-5
10.1002/chem.201705025
10.1021/ja00969a017
10.1021/je60038a025
10.1098/rspa.2012.0047
10.1021/ac60177a022
10.1007/s10570-021-04255-1
10.1021/cs400298n
10.1021/ja00444a023
10.1021/cs501388e
10.1021/acs.inorgchem.6b01702
10.1016/j.micromeso.2011.12.020
10.1039/b921284a
10.1002/cssc.201200703
10.3998/ark.5550190.0007.c15
10.1021/jo01046a528
10.1016/j.tetlet.2006.04.153
10.1021/jo8021988
10.1016/j.tet.2005.05.041
10.1016/S0040-4039(03)01089-X
10.1016/S0040-4039(01)99487-0
10.1021/ol060846t
10.1021/cr300182k
10.1016/B978-1-4831-9982-5.50017-8
10.1002/cctc.201901241
10.1021/ja00175a043
10.1021/ol034596h
ContentType Journal Article
Copyright 2022 Wiley‐VCH GmbH
Copyright_xml – notice: 2022 Wiley‐VCH GmbH
DBID AAYXX
CITATION
DOI 10.1002/cctc.202101730
DatabaseName CrossRef
DatabaseTitle CrossRef
DatabaseTitleList CrossRef


DeliveryMethod fulltext_linktorsrc
Discipline Chemistry
EISSN 1867-3899
EndPage n/a
ExternalDocumentID 10_1002_cctc_202101730
CCTC202101730
Genre article
GrantInformation_xml – fundername: Adisseo France SAS
GroupedDBID 05W
0R~
1OC
33P
4.4
5DZ
77Q
8-1
A00
AAESR
AAHHS
AAIHA
AANLZ
AAXRX
AAZKR
ABCUV
ABDBF
ACAHQ
ACCFJ
ACCZN
ACGFS
ACIWK
ACPOU
ACXBN
ACXQS
ADBBV
ADKYN
ADMGS
ADOZA
ADXAS
ADZMN
ADZOD
AEEZP
AEIGN
AENEX
AEQDE
AEUYR
AFBPY
AFFPM
AFGKR
AFZJQ
AHBTC
AITYG
AIURR
AIWBW
AJBDE
ALMA_UNASSIGNED_HOLDINGS
ALUQN
AMYDB
AZVAB
BDRZF
BFHJK
BMXJE
BRXPI
DCZOG
DRFUL
DRSTM
DU5
EBS
ESX
G-S
HGLYW
HZ~
I-F
LATKE
LEEKS
LITHE
LOXES
LUTES
LYRES
MEWTI
MXFUL
MXSTM
MY~
NNB
O9-
P2W
P4E
ROL
SUPJJ
TUS
WBKPD
WOHZO
WXSBR
WYJ
XV2
ZZTAW
AAYXX
CITATION
ID FETCH-LOGICAL-c3570-78272e9fbe92427c9ac0e6a78d64fb6051e994b19ac17053ccd95bb049fddfa13
ISSN 1867-3880
IngestDate Thu Oct 10 19:29:07 EDT 2024
Fri Aug 23 03:42:52 EDT 2024
Sat Aug 24 00:55:35 EDT 2024
IsDoiOpenAccess false
IsOpenAccess true
IsPeerReviewed true
IsScholarly true
Issue 8
Language English
LinkModel OpenURL
MergedId FETCHMERGED-LOGICAL-c3570-78272e9fbe92427c9ac0e6a78d64fb6051e994b19ac17053ccd95bb049fddfa13
ORCID 0000-0003-1760-6175
0000-0002-3074-2318
0000-0001-9657-1710
0000-0003-3296-7139
OpenAccessLink https://lirias.kuleuven.be/bitstream/20.500.12942/694696/3/Establishing%20the%20Reaction%20Pathways%20of%20the%20Catalytic%20Conversion%20of%20Erythrulose%20to%20Sulphides%20of%20Alpha%e2%80%90Hydroxy%20Thioesters%20and%20Esters%20accepted.pdf
PQID 2653050225
PQPubID 986343
PageCount 15
ParticipantIDs proquest_journals_2653050225
crossref_primary_10_1002_cctc_202101730
wiley_primary_10_1002_cctc_202101730_CCTC202101730
PublicationCentury 2000
PublicationDate April 22, 2022
PublicationDateYYYYMMDD 2022-04-22
PublicationDate_xml – month: 04
  year: 2022
  text: April 22, 2022
  day: 22
PublicationDecade 2020
PublicationPlace Weinheim
PublicationPlace_xml – name: Weinheim
PublicationTitle ChemCatChem
PublicationYear 2022
Publisher Wiley Subscription Services, Inc
Publisher_xml – name: Wiley Subscription Services, Inc
References 2010; 12
2017; 7
1968; 68
2013; 3
2006; 31
2019; 11
2021; 28
2019; 12
2014; 26
2005; 21
2011; 13
1975; 53
2005; 61
2012; 14
1961; 33
2008; 73
2013; 5
2013; 6
1959; 1
1885; 18
1968; 13
2012; 134
2007; 170
2019; 21
1950; 72
2014; 16
1978; 100
2013; 113
2003; 5
2006; 2006
2014; 7
1962; 84
2014; 98
2003; 44
2015; 5
2010; 328
2006; 8
2007
2004
2016; 18
2012; 468
1949; 71
1963; 28
1981; 67
2018; 24
2016; 55
1999
2004; 10
2012; 153
1998; 39
2015; 431
2015; 112
2006; 47
2017; 19
2016
1961
1977; 99
2015
2014
1990; 112
2009; 2
1966; 88
2001; 2001
2016; 9
e_1_2_9_52_1
e_1_2_9_50_1
e_1_2_9_10_1
e_1_2_9_35_1
e_1_2_9_56_1
e_1_2_9_12_1
e_1_2_9_33_1
e_1_2_9_54_1
Ouellette R. J. (e_1_2_9_65_1) 2015
Campaigne E. (e_1_2_9_46_1) 1961
e_1_2_9_14_1
e_1_2_9_39_1
e_1_2_9_16_1
e_1_2_9_37_1
e_1_2_9_58_1
e_1_2_9_18_1
e_1_2_9_41_1
e_1_2_9_64_1
e_1_2_9_20_1
e_1_2_9_62_1
e_1_2_9_22_1
Burgess J. (e_1_2_9_44_1) 1999
e_1_2_9_45_1
e_1_2_9_24_1
e_1_2_9_43_1
e_1_2_9_66_1
e_1_2_9_8_1
Jencks W. P. (e_1_2_9_51_1) 2007
e_1_2_9_6_1
e_1_2_9_4_1
e_1_2_9_60_1
e_1_2_9_2_1
e_1_2_9_26_1
e_1_2_9_49_1
e_1_2_9_28_1
e_1_2_9_47_1
e_1_2_9_30_1
e_1_2_9_53_1
Vollhardt P. (e_1_2_9_61_1) 2014
e_1_2_9_11_1
e_1_2_9_34_1
e_1_2_9_57_1
e_1_2_9_13_1
e_1_2_9_32_1
e_1_2_9_55_1
e_1_2_9_15_1
e_1_2_9_38_1
e_1_2_9_17_1
e_1_2_9_36_1
e_1_2_9_59_1
e_1_2_9_19_1
e_1_2_9_42_1
e_1_2_9_63_1
Dusselier M. (e_1_2_9_3_1) 2014
e_1_2_9_40_1
e_1_2_9_21_1
e_1_2_9_23_1
e_1_2_9_7_1
e_1_2_9_5_1
e_1_2_9_1_1
e_1_2_9_9_1
e_1_2_9_25_1
e_1_2_9_27_1
e_1_2_9_48_1
e_1_2_9_29_1
Sadaba Zubiri I. (e_1_2_9_31_1) 2016
References_xml – volume: 153
  start-page: 55
  year: 2012
  end-page: 58
  publication-title: Microporous Mesoporous Mater.
– volume: 13
  start-page: 386
  year: 1968
  end-page: 389
  publication-title: J. Chem. Eng. Data
– start-page: WO2016174231
  year: 2016
– volume: 55
  start-page: 9461
  year: 2016
  end-page: 9470
  publication-title: Inorg. Chem.
– volume: 88
  start-page: 3982
  year: 1966
  end-page: 3995
  publication-title: J. Am. Chem. Soc.
– volume: 328
  start-page: 602
  year: 2010
  end-page: 605
  publication-title: Science
– volume: 5
  start-page: 569
  year: 2013
  end-page: 575
  publication-title: ChemCatChem
– volume: 44
  start-page: 5115
  year: 2003
  end-page: 5119
  publication-title: Tetrahedron Lett.
– start-page: 1
  year: 2014
  end-page: 40
– volume: 5
  start-page: 928
  year: 2015
  end-page: 940
  publication-title: ACS Catal.
– volume: 7
  start-page: 1833
  year: 2014
  end-page: 1846
  publication-title: ChemSusChem
– volume: 5
  start-page: 5803
  year: 2015
  end-page: 5811
  publication-title: ACS Catal.
– volume: 12
  start-page: 1083
  year: 2010
  end-page: 1089
  publication-title: Green Chem.
– volume: 8
  start-page: 2433
  year: 2006
  end-page: 2436
  publication-title: Org. Lett.
– volume: 19
  start-page: 5012
  year: 2017
  end-page: 5040
  publication-title: Green Chem.
– volume: 7
  start-page: 985
  year: 2017
  end-page: 996
  publication-title: RSC Adv.
– volume: 6
  start-page: 831
  year: 2013
  end-page: 839
  publication-title: ChemSusChem
– volume: 100
  start-page: 5892
  year: 1978
  end-page: 5904
  publication-title: J. Am. Chem. Soc.
– volume: 67
  start-page: 207
  year: 1981
  end-page: 217
  publication-title: J. Catal.
– year: 2014
– volume: 1
  start-page: 22
  year: 1959
  end-page: 26
  publication-title: Tetrahedron Lett.
– volume: 24
  start-page: 7092
  year: 2018
  end-page: 7107
  publication-title: Chem. A Eur. J.
– volume: 72
  start-page: 3021
  year: 1950
  end-page: 3025
  publication-title: J. Am. Chem. Soc.
– volume: 68
  start-page: 449
  year: 1968
  end-page: 523
  publication-title: Chem. Rev.
– volume: 28
  start-page: 11665
  year: 2021
  end-page: 11678
  publication-title: Cellulose
– start-page: 134
  year: 1961
  end-page: 145
– volume: 98
  start-page: 9893
  year: 2014
  end-page: 9914
  publication-title: Appl. Microbiol. Biotechnol.
– year: 2004
– volume: 2006
  start-page: 130
  year: 2006
  end-page: 137
  publication-title: Arkivoc
– volume: 53
  start-page: 898
  year: 1975
  end-page: 906
  publication-title: Can. J. Chem.
– start-page: 63
  year: 2007
  end-page: 128
– volume: 112
  start-page: 11777
  year: 2015
  end-page: 11782
  publication-title: Proc. Natl. Acad. Sci. USA
– volume: 18
  start-page: 883
  year: 1885
  end-page: 892
  publication-title: Ber. Dtsch. Chem. Ges.
– volume: 47
  start-page: 4573
  year: 2006
  end-page: 4576
  publication-title: Tetrahedron Lett.
– volume: 84
  start-page: 16
  year: 1962
  end-page: 24
  publication-title: J. Am. Chem. Soc.
– volume: 16
  start-page: 516
  year: 2014
  end-page: 547
  publication-title: Green Chem.
– volume: 28
  start-page: 3246
  year: 1963
  end-page: 3248
  publication-title: J. Org. Chem.
– volume: 21
  start-page: 2716
  year: 2005
  end-page: 2718
  publication-title: Chem. Commun.
– volume: 13
  start-page: 1175
  year: 2011
  end-page: 1181
  publication-title: Green Chem.
– volume: 112
  start-page: 7050
  year: 1990
  end-page: 7051
  publication-title: J. Am. Chem. Soc.
– volume: 33
  start-page: 1196
  year: 1961
  end-page: 1201
  publication-title: Anal. Chem.
– volume: 61
  start-page: 7833
  year: 2005
  end-page: 7863
  publication-title: Tetrahedron
– volume: 21
  start-page: 993
  year: 2019
  end-page: 997
  publication-title: Org. Lett.
– volume: 5
  start-page: 2141
  year: 2003
  end-page: 2144
  publication-title: Org. Lett.
– volume: 2001
  start-page: 0983
  year: 2001
  end-page: 0985
  publication-title: Synlett
– volume: 10
  start-page: 484
  year: 2004
  end-page: 493
  publication-title: Chem. Eur. J.
– volume: 3
  start-page: 1786
  year: 2013
  end-page: 1800
  publication-title: ACS Catal.
– volume: 2
  start-page: 625
  year: 2009
  end-page: 627
  publication-title: ChemSusChem
– volume: 26
  start-page: 724
  year: 2014
  end-page: 744
  publication-title: Chem. Mater.
– volume: 31
  start-page: 487
  year: 2006
  end-page: 531
  publication-title: Prog. Polym. Sci.
– volume: 170
  start-page: 1222
  year: 2007
  end-page: 1227
  publication-title: Stud. Surf. Sci. Catal.
– start-page: 287
  year: 2015
  end-page: 314
– volume: 134
  start-page: 10089
  year: 2012
  end-page: 10101
  publication-title: J. Am. Chem. Soc.
– volume: 71
  start-page: 3349
  year: 1949
  end-page: 3351
  publication-title: J. Am. Chem. Soc.
– volume: 99
  start-page: 451
  year: 1977
  end-page: 464
  publication-title: J. Am. Chem. Soc.
– volume: 11
  start-page: 5077
  year: 2019
  end-page: 5084
  publication-title: ChemCatChem
– volume: 12
  start-page: 4775
  year: 2019
  end-page: 4779
  publication-title: ChemSusChem
– volume: 14
  start-page: 702
  year: 2012
  end-page: 706
  publication-title: Green Chem.
– volume: 18
  start-page: 5448
  year: 2016
  end-page: 5455
  publication-title: Green Chem.
– volume: 468
  start-page: 2000
  year: 2012
  end-page: 2016
  publication-title: Proc. Roy. Soc. A
– volume: 9
  start-page: 3054
  year: 2016
  end-page: 3061
  publication-title: ChemSusChem
– volume: 39
  start-page: 3189
  year: 1998
  end-page: 3192
  publication-title: Tetrahedron Lett.
– volume: 113
  start-page: 1499
  year: 2013
  end-page: 1597
  publication-title: Chem. Rev.
– volume: 431
  start-page: 289
  year: 2015
  end-page: 296
  publication-title: Inorg. Chim. Acta
– volume: 73
  start-page: 9522
  year: 2008
  end-page: 9524
  publication-title: J. Org. Chem.
– year: 1999
– ident: e_1_2_9_42_1
  doi: 10.1002/cber.188501801187
– start-page: 63
  volume-title: Prog. Phys. Org. Chem.
  year: 2007
  ident: e_1_2_9_51_1
  doi: 10.1002/9780470171813.ch2
  contributor:
    fullname: Jencks W. P.
– volume-title: Ions in Solution – Basic Principles of Chemical Interaction
  year: 1999
  ident: e_1_2_9_44_1
  contributor:
    fullname: Burgess J.
– ident: e_1_2_9_47_1
  doi: 10.1002/chem.200305407
– ident: e_1_2_9_35_1
  doi: 10.1021/cm402180t
– ident: e_1_2_9_6_1
  doi: 10.1039/C6RA26708D
– ident: e_1_2_9_30_1
  doi: 10.1007/s00253-014-6156-y
– ident: e_1_2_9_60_1
  doi: 10.1021/cr60254a003
– ident: e_1_2_9_1_1
  doi: 10.2172/15008859
– ident: e_1_2_9_14_1
  doi: 10.1039/c0gc00923g
– ident: e_1_2_9_18_1
  doi: 10.1073/pnas.1516466112
– ident: e_1_2_9_20_1
  doi: 10.1039/c2gc16202d
– ident: e_1_2_9_52_1
  doi: 10.1139/v75-125
– ident: e_1_2_9_56_1
  doi: 10.1002/cssc.201400040
– ident: e_1_2_9_48_1
  doi: 10.1021/ja00860a005
– ident: e_1_2_9_58_1
  doi: 10.1021/ja01163a061
– volume-title: Organic Chemistry. Structure and Function
  year: 2014
  ident: e_1_2_9_61_1
  contributor:
    fullname: Vollhardt P.
– ident: e_1_2_9_62_1
  doi: 10.1021/ja01178a021
– ident: e_1_2_9_5_1
  doi: 10.1039/C7GC02040F
– ident: e_1_2_9_57_1
  doi: 10.1021/ja00486a048
– start-page: 287
  volume-title: Princ. Org. Chem.
  year: 2015
  ident: e_1_2_9_65_1
  doi: 10.1016/B978-0-12-802444-7.00011-2
  contributor:
    fullname: Ouellette R. J.
– ident: e_1_2_9_17_1
  doi: 10.1021/ja301678w
– ident: e_1_2_9_32_1
  doi: 10.1021/acs.orglett.8b03986
– ident: e_1_2_9_45_1
  doi: 10.1016/j.progpolymsci.2006.03.001
– ident: e_1_2_9_16_1
  doi: 10.1016/j.ica.2015.04.011
– ident: e_1_2_9_23_1
  doi: 10.1021/acscatal.5b01344
– ident: e_1_2_9_64_1
  doi: 10.1002/cssc.201901742
– ident: e_1_2_9_2_1
  doi: 10.1039/c3gc41492b
– ident: e_1_2_9_38_1
  doi: 10.1055/s-2001-14912
– ident: e_1_2_9_54_1
  doi: 10.1016/0021-9517(81)90272-4
– ident: e_1_2_9_19_1
  doi: 10.1002/cssc.200900099
– ident: e_1_2_9_24_1
  doi: 10.1039/C6GC01556E
– ident: e_1_2_9_21_1
  doi: 10.1002/cctc.201200476
– ident: e_1_2_9_55_1
  doi: 10.1002/cssc.201600757
– ident: e_1_2_9_7_1
  doi: 10.1039/b501964h
– ident: e_1_2_9_26_1
  doi: 10.1016/S0040-4039(98)00456-0
– ident: e_1_2_9_12_1
  doi: 10.1126/science.1183990
– ident: e_1_2_9_8_1
  doi: 10.1016/S0167-2991(07)80981-5
– ident: e_1_2_9_25_1
  doi: 10.1002/chem.201705025
– ident: e_1_2_9_41_1
  doi: 10.1021/ja00969a017
– ident: e_1_2_9_49_1
  doi: 10.1021/je60038a025
– ident: e_1_2_9_15_1
  doi: 10.1098/rspa.2012.0047
– ident: e_1_2_9_59_1
  doi: 10.1021/ac60177a022
– ident: e_1_2_9_29_1
  doi: 10.1007/s10570-021-04255-1
– ident: e_1_2_9_22_1
  doi: 10.1021/cs400298n
– ident: e_1_2_9_66_1
  doi: 10.1021/ja00444a023
– start-page: 1
  volume-title: Sel. Catal. Renew. Feed. Chem. Top. Curr. Chem.
  year: 2014
  ident: e_1_2_9_3_1
  contributor:
    fullname: Dusselier M.
– ident: e_1_2_9_13_1
  doi: 10.1021/cs501388e
– ident: e_1_2_9_33_1
  doi: 10.1021/acs.inorgchem.6b01702
– ident: e_1_2_9_10_1
  doi: 10.1016/j.micromeso.2011.12.020
– ident: e_1_2_9_9_1
  doi: 10.1039/b921284a
– ident: e_1_2_9_11_1
  doi: 10.1002/cssc.201200703
– ident: e_1_2_9_40_1
  doi: 10.3998/ark.5550190.0007.c15
– ident: e_1_2_9_50_1
  doi: 10.1021/jo01046a528
– ident: e_1_2_9_28_1
  doi: 10.1016/j.tetlet.2006.04.153
– ident: e_1_2_9_43_1
  doi: 10.1021/jo8021988
– ident: e_1_2_9_63_1
  doi: 10.1016/j.tet.2005.05.041
– ident: e_1_2_9_37_1
  doi: 10.1016/S0040-4039(03)01089-X
– ident: e_1_2_9_53_1
  doi: 10.1016/S0040-4039(01)99487-0
– ident: e_1_2_9_39_1
  doi: 10.1021/ol060846t
– ident: e_1_2_9_4_1
  doi: 10.1021/cr300182k
– start-page: 134
  volume-title: Org. Sulfur Compd.
  year: 1961
  ident: e_1_2_9_46_1
  doi: 10.1016/B978-1-4831-9982-5.50017-8
  contributor:
    fullname: Campaigne E.
– ident: e_1_2_9_34_1
  doi: 10.1002/cctc.201901241
– ident: e_1_2_9_27_1
  doi: 10.1021/ja00175a043
– start-page: WO2016174231
  volume-title: A Process for the Preparation of Methionine Alpha-Hydroxy Analogues from Sugars and Derivatives Thereof
  year: 2016
  ident: e_1_2_9_31_1
  contributor:
    fullname: Sadaba Zubiri I.
– ident: e_1_2_9_36_1
  doi: 10.1021/ol034596h
SSID ssj0069375
Score 2.3819087
Snippet Sulphides of alpha‐hydroxy thioesters and esters (SAH(T)Es) are important fine chemicals and have great potential as platform molecules. SAH(T)Es are typically...
Abstract Sulphides of alpha‐hydroxy thioesters and esters (SAH(T)Es) are important fine chemicals and have great potential as platform molecules. SAH(T)Es are...
SourceID proquest
crossref
wiley
SourceType Aggregation Database
Publisher
SubjectTerms alpha-hydroxy esters
biomass
Carbohydrates
Catalytic converters
Chemical synthesis
Conversion
Esters
Fine chemicals
homogeneous catalysis
NMR
Nuclear magnetic resonance
Selectivity
Sulfides
sulphides
tetroses
Thioesters
Title Establishing the Reaction Pathways of the Catalytic Conversion of Erythrulose to Sulphides of Alpha‐Hydroxy Thioesters and Esters
URI https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fcctc.202101730
https://www.proquest.com/docview/2653050225
Volume 14
hasFullText 1
inHoldings 1
isFullTextHit
isPrint
link http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV3NjtMwELZK9wAXxK8ouyAfkDigQOvYSXNsQ6tqtdpdQYp6i2LHgaKqQWmqVTkh8QK8CC_FkzDjJG4qrYDlkqa25Laer_bM5PM3hLzgDAuHgOemtXAdnijXkUmgHI8pLDIpgiw1LN9zbzbnpwux6HR-tlhL21K-Vl-vPVfyP1aFNrArnpK9gWXtoNAA92BfuIKF4fpPNp6Aa2ezSOhBvtN16e9LcOyukt2moQCEmKXZoThriDRzkyMzpMJiV34qtitkrYMX-h656su0EqId4TFcS4aY7VJkvGChz9yoK1TizhNz23ZxUYIAPg5fbPpGFx-XOZ4DS3UBvmYz5gjQubL7gik9vvy8qXNCp3m-sZycMfz6Vx9gLZpts0xbVshl9Zwf8GmyQxerJW7z7UwGBMF97jB2g_WytU4PYX1HHZtqG2u3VfWW7OLOWyAeXrtnVBq0ShlFS4ZLVP2k6ECc-_wins7PzuJosohukSPmB0J0ydFo_HY8bbZ-D3w95Mzab9eohPbZm8PxD72gfWjTDpCMhxPdI3fr0ISOKpzdJx29fkBuh01FwIfkextvFGBFG7zRBm80z0yHxRvd4w37WnijZU4t3rDP4O3Xtx810ugeaRSQRiukPSLz6SQKZ05dxMNRrvCRrcp8poNMaoj0ma-CRPW1l_jD1OOZhGB6oIOAywG0o7KTq1QaCCkhcM3SNEsG7mPSXedr_YRQ7g-V5EIrhhpDQiY80QOeBVxI3_cGqkdeNpMaf6m0WuJKlZvFOP2xnf4eOWnmPK7_z5uYeQI2P8Cl6BFm7PCXUeIwjEL77umfxzwmd_aYPyHdstjqZ-DPlvJ5jaLf002kUQ
link.rule.ids 315,786,790,27955,27956
linkProvider EBSCOhost
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=Establishing+the+Reaction+Pathways+of+the+Catalytic+Conversion+of+Erythrulose+to+Sulphides+of+Alpha%E2%80%90Hydroxy+Thioesters+and+Esters&rft.jtitle=ChemCatChem&rft.au=Sergio+Calderon%E2%80%90Ardila&rft.au=Matthijssen%2C+Joost&rft.au=Bart+Van+Huffel&rft.au=P%C3%A9ruch%2C+Olivier&rft.date=2022-04-22&rft.pub=Wiley+Subscription+Services%2C+Inc&rft.issn=1867-3880&rft.eissn=1867-3899&rft.volume=14&rft.issue=8&rft_id=info:doi/10.1002%2Fcctc.202101730&rft.externalDBID=NO_FULL_TEXT
thumbnail_l http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=1867-3880&client=summon
thumbnail_m http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=1867-3880&client=summon
thumbnail_s http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=1867-3880&client=summon