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Bifunctional iminophosphorane-catalyzed enantioselective sulfa-michael addition to unactivated α,β-unsaturated amides

Abstract:

The first metal-free catalytic intermolecular enantioselective Michael addition to unactivated α,β-unsaturated amides is described. Consistently high enantiomeric excesses and yields were obtained over a wide range of alkyl thiol pronucleophiles and electrophiles under mild reaction conditions, enabled by a novel squaramide-based bifunctional iminophosphorane catalyst. Low catalyst loadings (2.0 mol %) were achieved on a decagram scale, demonstrating the scalability of the reaction. Computati...

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Publication status:
Published
Peer review status:
Peer reviewed

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Role:
Author
ORCID:
0000-0002-0516-1722
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Role:
Author
ORCID:
0000-0003-3641-7281
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Role:
Author
ORCID:
0000-0002-2039-4321
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Role:
Author
ORCID:
0000-0002-5128-1004
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Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Chemistry Research Laboratory
Role:
Author
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Name:
Engineering & Physical Sciences Research Council
Grant:
EP/J013501/1
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Name:
Honjo International Scholarship Foundation
Publisher:
American Chemical Society
Journal:
Journal of the American Chemical Society More from this journal
Volume:
144
Issue:
2
Pages:
1006-1015
Publication date:
2022-01-06
Acceptance date:
2021-12-10
DOI:
EISSN:
1520-5126
ISSN:
0002-7863
Pmid:
34990142
Language:
English
Keywords:
Pubs id:
1236432
Local pid:
pubs:1236432
Deposit date:
2022-03-16

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