Asymmetric Diels-Alder Reactions of Chiral Cyclopropylidene Imide Dienophiles: Preparation of gem-Dimethyl-and Spirocyclopropane Norbornyl Carboxylic Acids

…, GR Humphrey, M Journet, AE McKeown

Index: Kuethe, Jeffrey T.; Zhao, Dalian; Humphrey, Guy R.; Journet, Michel; McKeown, Arlene E. Journal of Organic Chemistry, 2006 , vol. 71, # 5 p. 2192 - 2195

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Citation Number: 18

Abstract

A highly efficient strategy has been developed for the rapid asymmetric synthesis of gem- dimethyl and spirocyclopropyl norbornyl carboxylic acids. The key transformation involved the unprecedented asymmetric Diels-Alder reaction of highly reactive β, β-cyclopropyl-α, β- unstaturated N-acyloxazolidinones with cyclopentadiene affording the adducts in high yield and de.