Enoldiazosulfones for Highly Enantioselective [3 + 3]-Cycloaddition with Nitrones Catalyzed by Copper(I) with Chiral BOX Ligands

Frady G Adly; Kostiantyn O Marichev; Joseph A Jensen; Hadi Arman; Michael P Doyle

doi:10.1021/acs.orglett.8b03421

Enoldiazosulfones for Highly Enantioselective [3 + 3]-Cycloaddition with Nitrones Catalyzed by Copper(I) with Chiral BOX Ligands

Org Lett. 2019 Jan 4;21(1):40-44. doi: 10.1021/acs.orglett.8b03421. Epub 2018 Dec 14.

Authors

Frady G Adly^{1

2}, Kostiantyn O Marichev¹, Joseph A Jensen¹, Hadi Arman¹, Michael P Doyle¹

Affiliations

¹ Department of Chemistry , University of Texas at San Antonio , San Antonio , Texas 78249 , United States.
² Faculty of Science and Technology , University of Canberra , Canberra , Australian Capital Territory 2601 , Australia.

PMID: 30550288
DOI: 10.1021/acs.orglett.8b03421

Abstract

Enoldiazosulfones undergo [3 + 3]-cycloaddition with nitrones when catalyzed by copper(I) catalysts, but not with dirhodium(II) catalysts. Under mild reaction conditions with chiral bisoxazoline ligands, copper(I) catalysts produce 1,2-oxazine-sulfone derivatives in high yields and enantioselectivities. Dirhodium(II) catalysts form stable donor-acceptor cyclopropenes that undergo uncatalyzed [3 + 2]-cycloaddition reactions with nitrones.

Publication types

Research Support, U.S. Gov't, Non-P.H.S.
Research Support, Non-U.S. Gov't