Endo-benzonorbornen-2-ol as an efficient non-natural chiral auxiliary in the asymmetric aza-Diels–Alder reactions between cyclopentadiene and (1-phenylethyl)iminoacetates

Exo-2-azabicyclo[2.2.1]hept-5-enes were obtained by cycloaddition reactions between cyclopentadiene and protonated (S)- and (R)-1-phenylethylimines of (1R,endo)-benzonorbornen-2-yl glyoxylate. The non-natural (1R,endo)-benzonorbornen-2-ol proved to be an efficient chiral auxiliary in these asymmetri...

Full description

Saved in:
Bibliographic Details
Published inRSC advances Vol. 4; no. 101; pp. 57768 - 57772
Main Authors Sousa, Carlos A. D., Maestro, Miguel A., Garcia-Mera, Xerardo, Rodríguez-Borges, José E.
Format Journal Article
LanguageEnglish
Published 01.01.2014
Subjects
Adducts
Asymmetry
Chromatography
Cycloaddition
Cyclopentadiene
Optical properties
Optical rotation
X-rays
Online AccessGet full text

Cover

Abstract Exo-2-azabicyclo[2.2.1]hept-5-enes were obtained by cycloaddition reactions between cyclopentadiene and protonated (S)- and (R)-1-phenylethylimines of (1R,endo)-benzonorbornen-2-yl glyoxylate. The non-natural (1R,endo)-benzonorbornen-2-ol proved to be an efficient chiral auxiliary in these asymmetric aza-Diels-Alder reactions, which afforded only exo-cycloadducts with 1S : 1Rdiastereomer ic ratios of 15 : 85 for (S)-(1-phenylethyl)imine and 93 : 7 for (R)-(1-phenylethyl)imine. The obtained diastereoisomers were effortlessly and efficiently isolated using a chromatographic column. The absolute configuration of all the formed adducts was unequivocally assigned through NMR, specific optical rotation and X-ray data.
AbstractList Exo-2-azabicyclo[2.2.1]hept-5-enes were obtained by cycloaddition reactions between cyclopentadiene and protonated (S)- and (R)-1-phenylethylimines of (1R,endo)-benzonorbornen-2-yl glyoxylate. The non-natural (1R,endo)-benzonorbornen-2-ol proved to be an efficient chiral auxiliary in these asymmetric aza-Diels-Alder reactions, which afforded only exo-cycloadducts with 1S : 1Rdiastereomer ic ratios of 15 : 85 for (S)-(1-phenylethyl)imine and 93 : 7 for (R)-(1-phenylethyl)imine. The obtained diastereoisomers were effortlessly and efficiently isolated using a chromatographic column. The absolute configuration of all the formed adducts was unequivocally assigned through NMR, specific optical rotation and X-ray data.
Author Maestro, Miguel A.
Sousa, Carlos A. D.
Garcia-Mera, Xerardo
Rodríguez-Borges, José E.
Author_xml – sequence: 1
  givenname: Carlos A. D.
  surname: Sousa
  fullname: Sousa, Carlos A. D.
– sequence: 2
  givenname: Miguel A.
  surname: Maestro
  fullname: Maestro, Miguel A.
– sequence: 3
  givenname: Xerardo
  surname: Garcia-Mera
  fullname: Garcia-Mera, Xerardo
– sequence: 4
  givenname: José E.
  surname: Rodríguez-Borges
  fullname: Rodríguez-Borges, José E.
BookMark eNpNUc1qVDEYDVKhtXbTJ8iyFaJJbprMXQ7TqQoFQXR9yU2-MJHcL2OSob1d-Q59DZ_KJ_HWCvptzrc4P3DOK3KEGYGQc8HfCt717zbq81oIobrtC3IiudJMct0f_fcfk7Nav_Hl9JWQWpyQn1v0mY2ADxlzGXNBQCZZTtRWapFCCNFFwEaXMIa2HYpN1O3iE9jDfUzRlplGpG0Hi2aeJmglOmofLLuOkOqvH4_r5KHQAta1mLHSEdodAFI3u5T3i7n1S8QiR08vBNvvAOcEbTenyzhFzNZBsw3qa_Iy2FTh7C-ekq832y-bD-z20_uPm_Utc1KrxkbjVXBeXgXdBTv2oEdlvHaqV26lXG-CNXqlOxVAKdsb03PPYSX9KI0UPe9OycWz777k7weobZhidZCSRciHOgjTcW64-UN980x1JddaIAz7EqelkkHw4WmV4d8q3W_ovIWu
CitedBy_id crossref_primary_10_1002_chin_201517080
crossref_primary_10_1021_acs_chemrev_7b00064
crossref_primary_10_1039_C6QO00330C
crossref_primary_10_1039_C9QO00957D
Cites_doi 10.1016/S0957-4166(00)00454-7
10.1016/j.tet.2013.03.033
10.1002/jlac.1991199101180
10.1016/S0957-4166(02)00048-4
10.1016/j.tet.2011.06.097
10.1016/S0040-4020(01)81187-X
10.1016/S0040-4020(01)89258-9
10.1016/S0957-4166(02)00127-1
10.1016/S0957-4166(01)00356-1
10.1021/ja00249a066
10.1016/S0957-4166(01)00079-9
10.1016/j.tetlet.2011.12.037
10.1016/S0957-4166(97)00305-4
10.1016/j.tetlet.2006.08.077
10.1016/j.tet.2006.06.118
10.1039/C39940002543
10.1021/cr00013a010
10.1016/S0040-4039(01)01000-0
10.1016/j.cplett.2009.06.009
10.1021/jo962074s
10.1039/P19910001337
10.1021/ja00856a074
10.1016/0040-4039(90)80136-A
10.1039/c39920000786
10.1016/S0040-4039(00)00594-3
10.1016/S0040-4039(00)97035-7
10.1016/S0040-4039(02)02599-6
10.1016/S0040-4039(00)86702-7
10.1016/S0040-4039(98)01102-2
10.1016/S0031-9422(00)95163-X
ContentType Journal Article
DBID AAYXX
CITATION
7SR
8BQ
8FD
JG9
DOI 10.1039/C4RA11143E
DatabaseName CrossRef
Engineered Materials Abstracts
METADEX
Technology Research Database
Materials Research Database
DatabaseTitle CrossRef
Materials Research Database
Engineered Materials Abstracts
Technology Research Database
METADEX
DatabaseTitleList Materials Research Database
DeliveryMethod fulltext_linktorsrc
Discipline Chemistry
EISSN 2046-2069
EndPage 57772
ExternalDocumentID 10_1039_C4RA11143E
GroupedDBID -JG
0-7
0R~
53G
AAEMU
AAFWJ
AAHBH
AAIWI
AAJAE
AARTK
AAWGC
AAXHV
AAYXX
ABASK
ABEMK
ABGFH
ABPDG
ABXOH
ACGFS
ADBBV
ADMRA
AEFDR
AENEX
AESAV
AETIL
AFLYV
AFPKN
AFVBQ
AGEGJ
AGRSR
AGSTE
AHGCF
AKBGW
ALMA_UNASSIGNED_HOLDINGS
ANBJS
ANUXI
APEMP
ASKNT
AUDPV
AUNWK
BCNDV
BLAPV
BSQNT
C6K
CITATION
EBS
ECGLT
EE0
EF-
EJD
GROUPED_DOAJ
H13
HZ~
H~N
J3G
J3H
J3I
M~E
O9-
OK1
PGMZT
R7C
R7G
RAOCF
RCNCU
ROYLF
RPM
RPMJG
RRC
RSCEA
RVUXY
SLH
SMJ
YAE
ZCN
7SR
8BQ
8FD
JG9
ID FETCH-LOGICAL-c264t-b7d4fcd25f63fab9e6b47d6c494c84c97fa768634fe44a97790d0e82db2721903
ISSN 2046-2069
IngestDate Fri Oct 25 22:54:48 EDT 2024
Fri Aug 23 01:41:14 EDT 2024
IsPeerReviewed true
IsScholarly true
Issue 101
Language English
LinkModel OpenURL
MergedId FETCHMERGED-LOGICAL-c264t-b7d4fcd25f63fab9e6b47d6c494c84c97fa768634fe44a97790d0e82db2721903
Notes ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
PQID 1730070790
PQPubID 23500
PageCount 5
ParticipantIDs proquest_miscellaneous_1730070790
crossref_primary_10_1039_C4RA11143E
PublicationCentury 2000
PublicationDate 2014-01-01
PublicationDateYYYYMMDD 2014-01-01
PublicationDate_xml – month: 01
  year: 2014
  text: 2014-01-01
  day: 01
PublicationDecade 2010
PublicationTitle RSC advances
PublicationYear 2014
References Whitesell (C4RA11143E-(cit5)/*[position()=1]) 1992; 92
Szymanski (C4RA11143E-(cit11f)/*[position()=1]) 2001; 12
Herrmann (C4RA11143E-(cit6)/*[position()=1]) 1996; vol. E21f
Tararov (C4RA11143E-(cit12b)/*[position()=1]) 2002; 13
Agrofoglio (C4RA11143E-(cit9b)/*[position()=1]) 1994; 50
Caamaño (C4RA11143E-(cit7b)/*[position()=1]) 2000; 41
Bailey (C4RA11143E-(cit10c)/*[position()=1]) 1991
Fernández (C4RA11143E-(cit8b)/*[position()=1]) 2005; 2
Yu (C4RA11143E-(cit11d)/*[position()=1]) 1997; 62
Seyden-Penne (C4RA11143E-(cit1a)/*[position()=1]) 1995
Sousa (C4RA11143E-(cit9c)/*[position()=1]) 2012; 53
Corey (C4RA11143E-(cit3)/*[position()=1]) 1975; 97
Alves (C4RA11143E-(cit8c)/*[position()=1]) 2006; 47
Bailey (C4RA11143E-(cit11c)/*[position()=1]) 1994
Fernández (C4RA11143E-(cit7c)/*[position()=1]) 2001; 42
Hamley (C4RA11143E-(cit11b)/*[position()=1]) 1992
Bush (C4RA11143E-(cit9a)/*[position()=1]) 1993; 32
Bireau (C4RA11143E-(cit2)/*[position()=1]) 1988; 29
Waldmann (C4RA11143E-(cit10d)/*[position()=1]) 1991
Fernández (C4RA11143E-(cit13)/*[position()=1]) 2001; 12
Fernández (C4RA11143E-(cit7a)/*[position()=1]) 2000; 11
Roos (C4RA11143E-(cit1b)/*[position()=1]) 2002
García-Mera (C4RA11143E-(cit8f)/*[position()=1]) 2011; 67
Abraham (C4RA11143E-(cit10b)/*[position()=1]) 1992; 48
Ekegren (C4RA11143E-(cit12a)/*[position()=1]) 2002; 13
Green (C4RA11143E-(cit4)/*[position()=1]) 1987; 109
Maggini (C4RA11143E-(cit11a)/*[position()=1]) 1990; 31
Stella (C4RA11143E-(cit10a)/*[position()=1]) 1990; 31
Blanco (C4RA11143E-(cit8a)/*[position()=1]) 1998; 39
Sousa (C4RA11143E-(cit8g)/*[position()=1]) 2013; 69
Fernández (C4RA11143E-(cit14)/*[position()=1]) 2003; 44
Vale (C4RA11143E-(cit8d)/*[position()=1]) 2006; 62
Bauer (C4RA11143E-(cit11e)/*[position()=1]) 1997; 8
Teixeira (C4RA11143E-(cit8e)/*[position()=1]) 2009; 477
References_xml – volume: 11
  start-page: 4805
  year: 2000
  ident: C4RA11143E-(cit7a)/*[position()=1]
  publication-title: Tetrahedron: Asymmetry
  doi: 10.1016/S0957-4166(00)00454-7
  contributor:
    fullname: Fernández
– volume: 69
  start-page: 5048
  year: 2013
  ident: C4RA11143E-(cit8g)/*[position()=1]
  publication-title: Tetrahedron
  doi: 10.1016/j.tet.2013.03.033
  contributor:
    fullname: Sousa
– start-page: 1045
  year: 1991
  ident: C4RA11143E-(cit10d)/*[position()=1]
  publication-title: Liebigs Ann. Chem.
  doi: 10.1002/jlac.1991199101180
  contributor:
    fullname: Waldmann
– volume: 13
  start-page: 25
  year: 2002
  ident: C4RA11143E-(cit12b)/*[position()=1]
  publication-title: Tetrahedron: Asymmetry
  doi: 10.1016/S0957-4166(02)00048-4
  contributor:
    fullname: Tararov
– volume: 67
  start-page: 7162
  year: 2011
  ident: C4RA11143E-(cit8f)/*[position()=1]
  publication-title: Tetrahedron
  doi: 10.1016/j.tet.2011.06.097
  contributor:
    fullname: García-Mera
– volume: 48
  start-page: 9707
  year: 1992
  ident: C4RA11143E-(cit10b)/*[position()=1]
  publication-title: Tetrahedron
  doi: 10.1016/S0040-4020(01)81187-X
  contributor:
    fullname: Abraham
– volume: 50
  start-page: 10611
  year: 1994
  ident: C4RA11143E-(cit9b)/*[position()=1]
  publication-title: Tetrahedron
  doi: 10.1016/S0040-4020(01)89258-9
  contributor:
    fullname: Agrofoglio
– volume: 13
  start-page: 447
  year: 2002
  ident: C4RA11143E-(cit12a)/*[position()=1]
  publication-title: Tetrahedron: Asymmetry
  doi: 10.1016/S0957-4166(02)00127-1
  contributor:
    fullname: Ekegren
– volume: 12
  start-page: 1939
  year: 2001
  ident: C4RA11143E-(cit11f)/*[position()=1]
  publication-title: Tetrahedron: Asymmetry
  doi: 10.1016/S0957-4166(01)00356-1
  contributor:
    fullname: Szymanski
– volume: 109
  start-page: 4752
  year: 1987
  ident: C4RA11143E-(cit4)/*[position()=1]
  publication-title: J. Am. Chem. Soc.
  doi: 10.1021/ja00249a066
  contributor:
    fullname: Green
– volume: 12
  start-page: 365
  year: 2001
  ident: C4RA11143E-(cit13)/*[position()=1]
  publication-title: Tetrahedron: Asymmetry
  doi: 10.1016/S0957-4166(01)00079-9
  contributor:
    fullname: Fernández
– volume: 53
  start-page: 1029
  year: 2012
  ident: C4RA11143E-(cit9c)/*[position()=1]
  publication-title: Tetrahedron Lett.
  doi: 10.1016/j.tetlet.2011.12.037
  contributor:
    fullname: Sousa
– volume: 8
  start-page: 2619
  year: 1997
  ident: C4RA11143E-(cit11e)/*[position()=1]
  publication-title: Tetrahedron: Asymmetry
  doi: 10.1016/S0957-4166(97)00305-4
  contributor:
    fullname: Bauer
– volume: 47
  start-page: 7595
  year: 2006
  ident: C4RA11143E-(cit8c)/*[position()=1]
  publication-title: Tetrahedron Lett.
  doi: 10.1016/j.tetlet.2006.08.077
  contributor:
    fullname: Alves
– volume: 62
  start-page: 9475
  year: 2006
  ident: C4RA11143E-(cit8d)/*[position()=1]
  publication-title: Tetrahedron
  doi: 10.1016/j.tet.2006.06.118
  contributor:
    fullname: Vale
– start-page: 2543
  year: 1994
  ident: C4RA11143E-(cit11c)/*[position()=1]
  publication-title: J. Chem. Soc., Chem. Commun.
  doi: 10.1039/C39940002543
  contributor:
    fullname: Bailey
– volume: 92
  start-page: 953
  year: 1992
  ident: C4RA11143E-(cit5)/*[position()=1]
  publication-title: Chem. Rev.
  doi: 10.1021/cr00013a010
  contributor:
    fullname: Whitesell
– volume: 42
  start-page: 5239
  year: 2001
  ident: C4RA11143E-(cit7c)/*[position()=1]
  publication-title: Tetrahedron Lett.
  doi: 10.1016/S0040-4039(01)01000-0
  contributor:
    fullname: Fernández
– volume: 477
  start-page: 60
  year: 2009
  ident: C4RA11143E-(cit8e)/*[position()=1]
  publication-title: Chem. Phys. Lett.
  doi: 10.1016/j.cplett.2009.06.009
  contributor:
    fullname: Teixeira
– volume: 62
  start-page: 903
  year: 1997
  ident: C4RA11143E-(cit11d)/*[position()=1]
  publication-title: J. Org. Chem.
  doi: 10.1021/jo962074s
  contributor:
    fullname: Yu
– start-page: 1337
  year: 1991
  ident: C4RA11143E-(cit10c)/*[position()=1]
  publication-title: J. Chem. Soc., Perkin Trans. 1
  doi: 10.1039/P19910001337
  contributor:
    fullname: Bailey
– volume: 97
  start-page: 6908
  year: 1975
  ident: C4RA11143E-(cit3)/*[position()=1]
  publication-title: J. Am. Chem. Soc.
  doi: 10.1021/ja00856a074
  contributor:
    fullname: Corey
– volume: 2
  start-page: 319
  year: 2005
  ident: C4RA11143E-(cit8b)/*[position()=1]
  publication-title: Synlett
  contributor:
    fullname: Fernández
– volume: vol. E21f
  volume-title: Methods of the Organic Chemistry
  year: 1996
  ident: C4RA11143E-(cit6)/*[position()=1]
  contributor:
    fullname: Herrmann
– volume: 31
  start-page: 2603
  year: 1990
  ident: C4RA11143E-(cit10a)/*[position()=1]
  publication-title: Tetrahedron Lett.
  doi: 10.1016/0040-4039(90)80136-A
  contributor:
    fullname: Stella
– start-page: 786
  year: 1992
  ident: C4RA11143E-(cit11b)/*[position()=1]
  publication-title: J. Chem. Soc., Chem. Commun.
  doi: 10.1039/c39920000786
  contributor:
    fullname: Hamley
– volume: 41
  start-page: 4123
  year: 2000
  ident: C4RA11143E-(cit7b)/*[position()=1]
  publication-title: Tetrahedron Lett.
  doi: 10.1016/S0040-4039(00)00594-3
  contributor:
    fullname: Caamaño
– volume-title: Chiral Auxiliaries and Ligands in Asymmetric Synthesis
  year: 1995
  ident: C4RA11143E-(cit1a)/*[position()=1]
  contributor:
    fullname: Seyden-Penne
– volume: 31
  start-page: 6243
  year: 1990
  ident: C4RA11143E-(cit11a)/*[position()=1]
  publication-title: Tetrahedron Lett.
  doi: 10.1016/S0040-4039(00)97035-7
  contributor:
    fullname: Maggini
– volume: 44
  start-page: 431
  year: 2003
  ident: C4RA11143E-(cit14)/*[position()=1]
  publication-title: Tetrahedron Lett.
  doi: 10.1016/S0040-4039(02)02599-6
  contributor:
    fullname: Fernández
– volume-title: Compendium of Chiral Auxiliary Applications
  year: 2002
  ident: C4RA11143E-(cit1b)/*[position()=1]
  contributor:
    fullname: Roos
– volume: 29
  start-page: 2175
  year: 1988
  ident: C4RA11143E-(cit2)/*[position()=1]
  publication-title: Tetrahedron Lett.
  doi: 10.1016/S0040-4039(00)86702-7
  contributor:
    fullname: Bireau
– volume: 39
  start-page: 5663
  year: 1998
  ident: C4RA11143E-(cit8a)/*[position()=1]
  publication-title: Tetrahedron Lett.
  doi: 10.1016/S0040-4039(98)01102-2
  contributor:
    fullname: Blanco
– volume: 32
  start-page: 737
  year: 1993
  ident: C4RA11143E-(cit9a)/*[position()=1]
  publication-title: Phytochemistry
  doi: 10.1016/S0031-9422(00)95163-X
  contributor:
    fullname: Bush
SSID ssj0000651261
Score 2.116799
Snippet Exo-2-azabicyclo[2.2.1]hept-5-enes were obtained by cycloaddition reactions between cyclopentadiene and protonated (S)- and (R)-1-phenylethylimines of...
SourceID proquest
crossref
SourceType Aggregation Database
StartPage 57768
SubjectTerms Adducts
Asymmetry
Chromatography
Cycloaddition
Cyclopentadiene
Optical properties
Optical rotation
X-rays
Title Endo-benzonorbornen-2-ol as an efficient non-natural chiral auxiliary in the asymmetric aza-Diels–Alder reactions between cyclopentadiene and (1-phenylethyl)iminoacetates
URI https://search.proquest.com/docview/1730070790
Volume 4
hasFullText 1
inHoldings 1
isFullTextHit
isPrint
link http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV1Jb9NAFB6FcoALYhWlgAYBEiga8DK242MIKRVqitQmUm7WeGZMLbl2lUUiOfCDOPETeW-8poBUuGSxHEfx-_KWme-9j5BXPvdloBLBOA8440nisNh2PaaUg62ig9A2YjCTE_9oxj_PvXmv97PDWlqv4ndy-8e-kv-xKhwDu2KX7D9YtrkoHIDXYF94BAvD47VsPM5VwWKdb4u8WIAxc50zhxUZisfA_1ab8RC42Q81PjMjPHEayHmKT2L9Lc1S5MxVTEex3FxcoL6W7IutYB9TiJpsiCLefUgsZcmYq2ldciMzFN5aGcZYuQWBI58YUsY2gIXzTfbaCVEyrBBSm4y2mwefno1q-kGT1J8V66WoSChZsexMipwIiF1lQ84k_brWWbsC-wm1kASbaKOX1J9jP7Uq2m0ktcAPbNkHXPpv9jyq_otqtcPmndUObbyiAwU9gKDUd6ldOO8itTq9dMheEJSyPVV0h_elVNBvocNycfKq5AsB7p-7ug2QNSng5Et0ODs-jqbj-fQGuemAa0OfOvnerupBQmdDTVrPwXXD9-0FdzOf3cBvspnpXXKnKkPosMTUPdLT-X1ya1Sr_z0gP_6GLSqWVOS0wRbtYIuW2KINtmiaU8AWbbFFr2CLNtiiFbboFWzBtyn6ZgdZb3dw9ZDMDsfT0RGrdD2YhPR7xeJA8UQqx0t8NxFxqP2YB8qXPORywGUYJAKM5rs80ZyLECdiKksPHBU7AQRYy31E9uC36ceE-l4SWnIASSi4GuT1KWVJP4aawvc0FBf75GV9z6PLcnxLZGgXbhiN-OnQWGa8T17U5ojgNuOWmcg1gD6yUc4Bh0haT65xzgG53WL2KdlbLdb6GeSsq_i5gckvKKGjNg
link.rule.ids 315,783,787,27936,27937
linkProvider ISSN International Centre
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=Endo-benzonorbornen-2-ol+as+an+efficient+non-natural+chiral+auxiliary+in+the+asymmetric+aza-Diels-Alder+reactions+between+cyclopentadiene+and+%281-phenylethyl%29iminoacetates&rft.jtitle=RSC+advances&rft.au=Sousa%2C+Carlos+AD&rft.au=Maestro%2C+Miguel+A&rft.au=Garcia-Mera%2C+Xerardo&rft.au=Rodriguez-Borges%2C+Jose+E&rft.date=2014-01-01&rft.eissn=2046-2069&rft.volume=4&rft.issue=101&rft.spage=57768&rft.epage=57772&rft_id=info:doi/10.1039%2Fc4ra11143e&rft.externalDBID=NO_FULL_TEXT
thumbnail_l http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=2046-2069&client=summon
thumbnail_m http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=2046-2069&client=summon
thumbnail_s http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=2046-2069&client=summon