Gold(I)-catalyzed Enantioselective [3+2] and [3+3] Cycloaddition Reactions of Propargyl Acetals/ketals

Overview

Journal Tetrahedron

Specialty Chemistry

Date 2015 Aug 15

PMID 26273112

Citations 1

Authors

Cristina Navarro

Nathan D Shapiro

Maurizio Bernasconi

Takahiro Horibe

F Dean Toste

Affiliations

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Abstract

An asymmetric gold(I)-catalyzed [3+2] cycloaddition of propargyl acetals/ketals and aldehydes is reported, which proceeds via stepwise migration-fragmentation of acetals/ketals and cycloaddition of the in situ generated gold-carbenoid intermediate. Various functionalized 2, 5-dihydrofurans were obtained in good yields and high enantioselectivities. Furthermore, an example of the first gold(I) catalyzed [3+3] cycloaddition of secondary propargyl ketals and nitrones is presented.

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