Diastereoselective Synthesis of γ-Substituted 2-Butenolides via (CDC)-Rh-Catalyzed Intermolecular Hydroalkylation of Dienes with Silyloxyfurans.

Autor:	Goldfogel MJ; Department of Chemistry, The University of North Carolina at Chapel Hill , Chapel Hill, North Carolina 27599-3290, United States., Roberts CC; Department of Chemistry, The University of North Carolina at Chapel Hill , Chapel Hill, North Carolina 27599-3290, United States., Manan RS; Department of Chemistry, The University of North Carolina at Chapel Hill , Chapel Hill, North Carolina 27599-3290, United States., Meek SJ; Department of Chemistry, The University of North Carolina at Chapel Hill , Chapel Hill, North Carolina 27599-3290, United States.
Jazyk:	angličtina
Zdroj:	Organic letters [Org Lett] 2017 Jan 06; Vol. 19 (1), pp. 90-93. Date of Electronic Publication: 2016 Dec 20.
DOI:	10.1021/acs.orglett.6b03369
Abstrakt:	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.
Databáze:	MEDLINE
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