Enzymatic Resolution and Decarboxylative Functionalization of α-Sulfinyl Esters

Suraksha Gahalawat; Yesu Addepalli; Stephen P. Fink; Lakshmi Kasturi; Sanford D. Markowitz; Joseph M. Ready

doi:10.1002/chem.202302996

Enzymatic Resolution and Decarboxylative Functionalization of α-Sulfinyl Esters

Suraksha Gahalawat, Yesu Addepalli, Stephen P. Fink, Lakshmi Kasturi, Sanford D. Markowitz, Joseph M. Ready

Research output: Contribution to journal › Article › peer-review

Abstract

α-Sulfinyl esters can be readily prepared through thiol substitution of α-bromo esters followed by oxidation to the sulfoxide. Enzymatic resolution with lipoprotein lipase provides both the unreacted esters and corresponding α-sulfinyl carboxylic acids in high yields and enantiomeric ratios. Subsequent decarboxylative halogenation, dihalogenation, trihalogenation and cross-coupling gives rise to functionalized sulfoxides. The method has been applied to the asymmetric synthesis of a potent inhibitor of 15-prostaglandin dehydrogenase.

Original language	English (US)
Article number	e202302996
Journal	Chemistry - A European Journal
Volume	30
Issue number	7
DOIs	https://doi.org/10.1002/chem.202302996
State	Published - Feb 1 2024
Externally published	Yes

Keywords

decarboxylation
halogenation
lipase
resolution
sulfoxides

ASJC Scopus subject areas

Catalysis
General Chemistry
Organic Chemistry

Access to Document

10.1002/chem.202302996

Cite this

@article{76078d0991cd499fb4f4fc73ed109b7e,

title = "Enzymatic Resolution and Decarboxylative Functionalization of α-Sulfinyl Esters",

abstract = "α-Sulfinyl esters can be readily prepared through thiol substitution of α-bromo esters followed by oxidation to the sulfoxide. Enzymatic resolution with lipoprotein lipase provides both the unreacted esters and corresponding α-sulfinyl carboxylic acids in high yields and enantiomeric ratios. Subsequent decarboxylative halogenation, dihalogenation, trihalogenation and cross-coupling gives rise to functionalized sulfoxides. The method has been applied to the asymmetric synthesis of a potent inhibitor of 15-prostaglandin dehydrogenase.",

keywords = "decarboxylation, halogenation, lipase, resolution, sulfoxides",

author = "Suraksha Gahalawat and Yesu Addepalli and Fink, {Stephen P.} and Lakshmi Kasturi and Markowitz, {Sanford D.} and Ready, {Joseph M.}",

note = "Publisher Copyright: {\textcopyright} 2023 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.",

year = "2024",

month = feb,

day = "1",

doi = "10.1002/chem.202302996",

language = "English (US)",

volume = "30",

journal = "Chemistry - A European Journal",

issn = "0947-6539",

publisher = "Wiley-VCH Verlag",

number = "7",

}

TY - JOUR

T1 - Enzymatic Resolution and Decarboxylative Functionalization of α-Sulfinyl Esters

AU - Gahalawat, Suraksha

AU - Addepalli, Yesu

AU - Fink, Stephen P.

AU - Kasturi, Lakshmi

AU - Markowitz, Sanford D.

AU - Ready, Joseph M.

PY - 2024/2/1

Y1 - 2024/2/1

N2 - α-Sulfinyl esters can be readily prepared through thiol substitution of α-bromo esters followed by oxidation to the sulfoxide. Enzymatic resolution with lipoprotein lipase provides both the unreacted esters and corresponding α-sulfinyl carboxylic acids in high yields and enantiomeric ratios. Subsequent decarboxylative halogenation, dihalogenation, trihalogenation and cross-coupling gives rise to functionalized sulfoxides. The method has been applied to the asymmetric synthesis of a potent inhibitor of 15-prostaglandin dehydrogenase.

AB - α-Sulfinyl esters can be readily prepared through thiol substitution of α-bromo esters followed by oxidation to the sulfoxide. Enzymatic resolution with lipoprotein lipase provides both the unreacted esters and corresponding α-sulfinyl carboxylic acids in high yields and enantiomeric ratios. Subsequent decarboxylative halogenation, dihalogenation, trihalogenation and cross-coupling gives rise to functionalized sulfoxides. The method has been applied to the asymmetric synthesis of a potent inhibitor of 15-prostaglandin dehydrogenase.

KW - decarboxylation

KW - halogenation

KW - lipase

KW - resolution

KW - sulfoxides

UR - http://www.scopus.com/inward/record.url?scp=85179336182&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85179336182&partnerID=8YFLogxK

U2 - 10.1002/chem.202302996

DO - 10.1002/chem.202302996

M3 - Article

C2 - 37721804

AN - SCOPUS:85179336182

SN - 0947-6539

VL - 30

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 7

M1 - e202302996

ER -

Enzymatic Resolution and Decarboxylative Functionalization of α-Sulfinyl Esters

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this