Unexpected Catalytic Reactions of Silyl-protected Enol Diazoacetates with Nitrile Oxides That Form 5-arylaminofuran-2(3H)-one-4-carboxylates

Overview

Journal Org Lett

Publisher American Chemical Society

Specialties Biochemistry
Chemistry

Date 2012 Jan 26

PMID 22272728

Citations 8

Authors

Xinfang Xu

Dmitry Shabashov

Peter Y Zavalij

Michael P Doyle

Affiliations

Soon will be listed here.

Abstract

Silyl-protected enol diazoacetates undergo dirhodium(II)-catalyzed reactions with nitrile oxides to form acid-labile ketenimines via dipolar cycloaddition of nitrile oxides to a donor/acceptor cyclopropene and Lossen rearrangement of the dipolar adduct; acid catalysis converts the ketenimine to the furan product.

Citing Articles

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Xu X, Zavalij P, Doyle M Angew Chem Int Ed Engl. 2013; 52(48):12664-8.

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