Ruthenium-catalyzed two-component addition to form 1, 3-dienes: Optimization, scope, applications, and mechanism

BM Trost, AB Pinkerton, M Seidel

Index: Trost; Pinkerton; Seidel Journal of the American Chemical Society, 2001 , vol. 123, # 50 p. 12466 - 12476

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Citation Number: 94

Abstract

A two component coupling of an allene and an activated olefin to form 1, 3-dienes has been developed. The requisite allenes are synthesized either from terminal alkynes by a one carbon homologation using copper (I) iodide, paraformaldehyde, and diisopropylamine, via an ortho ester-Claisen rearrangement from a propargylic alcohol, or via a Wittig type reaction on a ketene generated in situ from an acid chloride. Mono-through ...