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Bifunctional iminophosphorane catalysed enantioselective sulfa-Michael addition of alkyl thiols to alkenyl benzimidazoles

Abstract:
The first enantioselective sulfa-Michael addition of alkyl thiols to alkenyl benzimidazoles, enabled by a bifunctional iminophosphorane (BIMP) organocatalyst, is described. The iminophosphorane moiety of the catalyst provides the required basicity to deprotonate the thiol nucleophile while the chiral scaffold and H-bond donor control facial selectivity. The reaction is broad in scope with respect to the thiol and benzimidazole reaction partners with the reaction proceeding in up to 98% yield and 96:4 er.
Publication status:
Published
Peer review status:
Peer reviewed

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Publisher copy:
10.1039/c8sc01804a

Authors


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Institution:
University of Oxford
Division:
MPLS Division
Department:
Chemistry
Role:
Author
More by this author
Institution:
University of Oxford
Division:
MPLS Division
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
More by this author
Institution:
University of Oxford
Division:
MPLS Division
Department:
Chemistry
Sub department:
Organic Chemistry
Oxford college:
St Hilda's College
Role:
Author
ORCID:
0000-0002-0104-4166
More from this funder
Name:
Engineering and Physical Sciences Research Council
Funding agency for:
Formica, M
Grant:
EP/L015838/1
More from this funder
Name:
National Science Foundation
More from this funder
Name:
University of Colorado Boulder and Colorado State University
More from this funder
Name:
Université Paris Descartes
More from this funder
Name:
Spanish Ministry of Education, Culture and Sports
Publisher:
Royal Society of Chemistry
Journal:
Chemical Science More from this journal
Volume:
9
Issue:
34
Pages:
6969-6974
Publication date:
2018-07-23
Acceptance date:
2018-07-12
DOI:
EISSN:
2041-6539
ISSN:
2041-6520
Keywords:
Pubs id:
pubs:916023
UUID:
uuid:0bcff2af-b6fc-4fd6-b6be-14c10c3f0a6c
Local pid:
pubs:916023
Source identifiers:
916023
Deposit date:
2018-09-11

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