Practical and highly stereoselective technology for preparation of enantiopure sulfoxides and sulfinamides utilizing activated and functionally differentiated N-sulfonyl-1,2,3-oxathiazolidine-2-oxide derivatives

A simple, general, and practical technology to prepare enantiopure 1,2,3-oxathiazolidine-2-oxide derivatives using chiral aryl N-sulfonyl aminoalcohol derivatives and thionyl chloride is reported. The versatility of these novel chiral building blocks (MIOO and TMPOO), was exemplified by the expedien...

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Bibliographic Details
Published inTetrahedron Vol. 61; no. 26; pp. 6386 - 6408
Main Authors Han, Zhengxu, Krishnamurthy, Dhileepkumar, Grover, Paul, Fang, Q. Kevin, Su, Xiping, Wilkinson, H. Scott, Lu, Zhi-Hui, Magiera, Daniel, Senanayake, Chris H.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 27.06.2005
Elsevier
Subjects
1,2,3-Oxathiazolidine-2-oxide
Chemistry
Chemistry, Organic
Chiral sulfinamide
Chiral sulfoxide
Physical Sciences
Science & Technology
1,2,3-Oxathiazolidine-2-oxide
Chiral sulfinamide
Chiral sulfoxide
SULFINIMINES
CATALYTIC ASYMMETRIC OXIDATION
GENERAL-ROUTE
REAGENTS
ESTERS
CHIRAL SULFOXIDES
DAG
TERT-BUTYL SULFOXIDES
SULFINYL CHLORIDES
chiral sulfinamide
chiral sulfoxide
1,2,3-oxathiazolidine-2-oxide
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Summary:A simple, general, and practical technology to prepare enantiopure 1,2,3-oxathiazolidine-2-oxide derivatives using chiral aryl N-sulfonyl aminoalcohol derivatives and thionyl chloride is reported. The versatility of these novel chiral building blocks (MIOO and TMPOO), was exemplified by the expedient production of a variety of unique chiral sulfoxides and valuable chiral sulfinamides in excellent yields and enantiopurities. Graphical Abstract
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2005.03.122