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Organocatalytic Enantioselective Sulfa-Michael Additions to α,β-Unsaturated Diazoketones

Journal of Organic Chemistry, 2022-03, Vol.87 (5), p.3482-3490 [Peer Reviewed Journal]

Publisher Copyright: © 2022 American Chemical Society. All rights reserved. ;ISSN: 0022-3263 ;ISSN: 1520-6904 ;EISSN: 1520-6904 ;DOI: 10.1021/acs.joc.1c03045 ;PMID: 35179890

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  • Title:
    Organocatalytic Enantioselective Sulfa-Michael Additions to α,β-Unsaturated Diazoketones
  • Author: Momo, Patricia B ; Mizobuchi, Eduardo F ; Echemendía, Radell ; Baddeley, Isabel ; Grayson, Matthew N ; Burtoloso, Antonio C B
  • Subjects: Organic Chemistry
  • Is Part Of: Journal of Organic Chemistry, 2022-03, Vol.87 (5), p.3482-3490
  • Description: Enantioselective sulfa-Michael additions to α,β unsaturated diazocarbonyl compounds have been developed. Quinine-derived squaramide was found to be the best catalyst to promote C-S bond formation in a highly stereoselective fashion for alkyl and aryl thiols. The easy-to-follow protocol allowed the preparation of 22 examples in enantiomeric ratios up to 97:3 and reaction yields up to 94%. The mechanism and origins of enantioselectivity were determined through density functional theory (DFT) calculations.
  • Language: English
  • Identifier: ISSN: 0022-3263
    ISSN: 1520-6904
    EISSN: 1520-6904
    DOI: 10.1021/acs.joc.1c03045
    PMID: 35179890
  • Source: Opus: University of Bath's Eprints IR
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