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

doi:10.1021/acs.orglett.6b03369

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 journal › Article › peer-review

20 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 language	English (US)
Pages (from-to)	90-93
Number of pages	4
Journal	Organic Letters
Volume	19
Issue number	1
DOIs	https://doi.org/10.1021/acs.orglett.6b03369
State	Published - Jan 6 2017
Externally published	Yes

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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10.1021/acs.orglett.6b03369

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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.",

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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: {\textcopyright} 2016 American Chemical Society.",

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AU - Goldfogel, Matthew J.

AU - Roberts, Courtney C.

AU - Manan, Rajith S.

AU - Meek, Simon J.

N1 - 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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Y1 - 2017/1/6

N2 - 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.

AB - 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.

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

Abstract

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