The Journal of organic chemistry

A Reductive-Coupling plus Nazarov Cyclization Sequence in the Asymmetric Synthesis of Five-Membered Carbocycles

DJ Kerr, JM White, BL Flynn

Index: Kerr, Daniel J.; White, Jonathan M.; Flynn, Bernard L. Journal of Organic Chemistry, 2010 , vol. 75, # 21 p. 7073 - 7084

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Citation Number: 26

Abstract

Palladium-mediated hydrostannylation of alkynoyl compounds is combined with Stille− Scott cross-coupling (reductive-coupling) to give one-pot access to divinyl and aryl vinyl ketones, which undergo Nazarov cyclization to give cyclopentenones upon treatment with acid. This reaction sequence has been studied with a variety of different substitution patterns, including the use of oxazolidinone auxiliaries to achieve torquoselectivity in the Nazarov cyclization. ...

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