Complete Regio- and Stereoselective Construction of Highly Substituted Silyl Enol Ethers by Three-Component Coupling

Three components for total control: Trisubstituted silyl enol ethers were prepared by three‐component coupling of α‐silyl α,β‐unsaturated ketones, organocopper reagents, and organic halides with complete regio‐ and stereoselectivity (see scheme). The reaction proceeded through a 1,3 migration of the...

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Veröffentlicht in:Angewandte Chemie (International ed.) 2010-09, Vol.49 (39), p.7089-7091
Hauptverfasser: Tsubouchi, Akira, Enatsu, Shouko, Kanno, Ryo, Takeda, Takeshi
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Sprache:eng
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Zusammenfassung:Three components for total control: Trisubstituted silyl enol ethers were prepared by three‐component coupling of α‐silyl α,β‐unsaturated ketones, organocopper reagents, and organic halides with complete regio‐ and stereoselectivity (see scheme). The reaction proceeded through a 1,3 migration of the silyl group via cyclic silicate intermediates, which controlled the configuration of the silyl enol ethers.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201003152