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

Patricia B Momo, Eduardo F Mizobuchi, Radell Echemendía, Isabel Baddeley, Matthew N Grayson, Antonio C B Burtoloso

Research output: Contribution to journalArticlepeer-review

Abstract

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.

Original languageEnglish
Pages (from-to)3482-3490
Number of pages9
JournalJournal of Organic Chemistry
Volume87
Issue number5
Early online date18 Feb 2022
DOIs
Publication statusPublished - 4 Mar 2022

ASJC Scopus subject areas

  • Organic Chemistry

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