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Diversity of products in the gold-catalyzed cyclization of 1-epoxy-1-alkynylcyclopropanes by using 1-oxyallyl cations
Journal article   Peer reviewed

Diversity of products in the gold-catalyzed cyclization of 1-epoxy-1-alkynylcyclopropanes by using 1-oxyallyl cations

Chun-Yao Yang, Min-Shiun Lin, Hsuan-Hung Liao and Rai-Shung Liu
Chemistry - A European Journal, Vol.16(9), pp.2696-2699
01/03/2010

Abstract

Alkynes Cycloaddition Epoxides Gold Oxycyclization
(Chemical Presented) A highly stereoselective AuCl 3 -catalyzed hydrative cyclization of 1-epoxy-1-alkynylcyclopropanes was observed for cis-epoxides. Since this cyclization produced 1-oxyallyl cations efficiently, we accomplished a two-step [4+2] annulation of epoxyalkynes with dienes and enones, to provide complex oxacyclic compounds with excellent diastereoselectivity (see scheme). © 2010 Wiley-VCH Verlag GmbH & Co. KGaA.

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