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

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5 Citations (SciVal)
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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

Bibliographical note

Funding Information:
A.C.B.B thanks FAPESP for financial support through grant numbers 2020/07147-0 and 2017/23329-9 in the form of a fellowship to P.B.M. (2015/22003-7), E.F.M. (2018/02920-3), and R.E. (2019/12300-5). We also thank the Capes for financial support in the form of Ph.D. fellowship to E.F.M., I.B., and M.N.G. thank the University of Bath for financial support. This research made use of the Balena High Performance Computing (HPC) Service at the University of Bath.

Publisher Copyright:
© 2022 American Chemical Society. All rights reserved.

ASJC Scopus subject areas

  • Organic Chemistry

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