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Asymmetric synthesis of trisubstituted tetrahydrothiophenes bearing a quaternary stereocenter via double Michael reaction involving dynamic kinetic resolution.

Authors
Type
Published Article
Journal
Organic Letters
1523-7052
Publisher
American Chemical Society
Publication Date
Volume
15
Issue
13
Pages
3436–3439
Identifiers
DOI: 10.1021/ol4014975
PMID: 23786495
Source
Medline
License
Unknown

Abstract

The stereoselective synthesis of highly functionalized tetrahydrothiophenes bearing three contiguous stereocenters, one of them quaternary, can be achieved by reacting trans-α-cyano-α,β-unsaturated ketones and trans-tert-butyl 4-mercapto-2-butenoate in the presence of a readily available amine thiourea. The products are obtained in high yield, good diastereoselectivity, and excellent enantioselectivity. The overall formation of tetrahydrothiophenes occurs via a cascade double Michael reaction involving a highly efficient process of dynamic kinetic resolution.

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