Diastereoselective synthesis of γ-substituted 2-butenolides via (CDC)-Rh-catalyzed intermolecular hydroalkylation of dienes with silyloxyfurans

Matthew J. Goldfogel, Courtney C. Roberts, Rajith S. Manan, Simon J. Meek

Research output: Contribution to journalArticlepeer-review

15 Scopus citations

Abstract

Catalytic intermolecular hydroalkylation of dienes with silyloxyfuran nucleophiles is reported. Reactions are catalyzed by 5 mol % of a (CDC)-Rh complex and proceed in up to 87% yield and 6:1 dr (syn/anti) to provide allylic butenolides bearing vicinal stereocenters. Reactions proceed with terminal aryl and alkyl dienes and with modified silyl enol ether nucleophiles including a thiophenone variant. Utility of the products is demonstrated in the synthesis of a polypropionate anti, syn-stereotriad.

Original languageEnglish (US)
Pages (from-to)90-93
Number of pages4
JournalOrganic Letters
Volume19
Issue number1
DOIs
StatePublished - Jan 6 2017
Externally publishedYes

Bibliographical note

Funding Information:
Financial support was provided by the University of North Carolina at Chapel Hill and the Petroleum Research Fund of the American Chemical Society (52447-DNI1).

Publisher Copyright:
© 2016 American Chemical Society.

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