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Published on: August 12, 2019
A Catalytic, Enantioselective Sulfamate Tethered Aza-Michael Cyclization
Harshit Joshi1, Abhijit Manna1, Someshwar Nagamalla1
1Department of Medicinal Chemistry, University of Kansas, Lawrence, Kansas 66047, United States.
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.
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