A reductive-coupling plus Nazarov cyclization sequence in the asymmetric synthesis of five-membered carbocycles

Daniel Kerr, Jonathan White, Bernard Flynn

Research output: Contribution to journalArticleResearchpeer-review

36 Citations (Scopus)

Abstract

Palladium-mediated hydrostannylation of alkynoyl compounds is combined with Stillea??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. Through a combination of good yields and moderate to good levels of stereochemical induction, this approach affords efficient, convergent, and asymmetric access to a variety of different cyclopentanoid systems.
Original languageEnglish
Pages (from-to)7073 - 7084
Number of pages12
JournalThe Journal of Organic Chemistry
Volume75
Issue number21
DOIs
Publication statusPublished - 2010

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