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

doi:10.1021/acs.joc.1c03045

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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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 language	English
Pages (from-to)	3482-3490
Number of pages	9
Journal	Journal of Organic Chemistry
Volume	87
Issue number	5
Early online date	18 Feb 2022
DOIs	https://doi.org/10.1021/acs.joc.1c03045
Publication status	Published - 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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10.1021/acs.joc.1c03045

JOC article - Sulfa Michael revised Accepted author manuscript, 1.6 MB

Cite this

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

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.",

author = "Momo, {Patricia B} and Mizobuchi, {Eduardo F} and Radell Echemend{\'i}a and Isabel Baddeley and Grayson, {Matthew N} and Burtoloso, {Antonio C B}",

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: {\textcopyright} 2022 American Chemical Society. All rights reserved.",

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doi = "10.1021/acs.joc.1c03045",

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T1 - Organocatalytic Enantioselective Sulfa-Michael Additions to α,β-Unsaturated Diazoketones

AU - Momo, Patricia B

AU - Mizobuchi, Eduardo F

AU - Echemendía, Radell

AU - Baddeley, Isabel

AU - Grayson, Matthew N

AU - Burtoloso, Antonio C B

N1 - 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.

PY - 2022/3/4

Y1 - 2022/3/4

N2 - 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.

AB - 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.

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

Abstract

Bibliographical note

ASJC Scopus subject areas

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