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

Frady G. Adly, Kostiantyn Marichev, Joseph Jensen, Hadi Arman, Michael Doyle

Research output: Contribution to journalArticle

6 Citations (Scopus)

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.
Original languageEnglish
Pages (from-to)40-44
Number of pages5
JournalOrganic Letters
Volume21
Issue number1
DOIs
Publication statusPublished - 4 Jan 2019

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