A Catalytic, Enantioselective Sulfamate Tethered -Michael Cyclization

Overview

Journal Org Lett

Publisher American Chemical Society

Specialties Biochemistry
Chemistry

Date 2024 Dec 11

PMID 39660506

Authors

Harshit Joshi

Abhijit Manna

Someshwar Nagamalla

Annu Anna Thomas

Shyam Sathyamoorthi

Affiliations

Soon will be listed here.

Abstract

We show the first examples of enantioselective cyclization reactions of tethered sulfamates onto pendant α,β-unsaturated esters, ketones, and thioesters. This reaction is promoted by a new chiral bifunctional guanidine catalyst and is operationally very simple. A variety of primary sulfamates and sulfamides were examined, and in many cases, products were delivered in excellent yields and enantiomeric ratios. With secondary sulfamates, kinetic resolutions were possible. The product oxathiazinanes are very useful chiral synthons.

Citing Articles

A Catalytic, Enantioselective Sulfamate Tethered -Michael Cyclization.

Joshi H, Manna A, Nagamalla S, Thomas A, Sathyamoorthi S Org Lett. 2024; 26(50):10708-10713.

PMID: 39660506 PMC: 11662505. DOI: 10.1021/acs.orglett.4c03558.

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