Tandem Asymmetric Cyclopropanation/Cope Rearrangement. A Highly Diastereoselective and Enantioselective Method for the Construction of 1,4-Cycloheptadienes

Tandem Asymmetric Cyclopropanation/Cope Rearrangement. A Highly Diastereoselective and Enantioselective Method for the Construction of 1,4-Cycloheptadienes

Decomposition of vinyldiazoacetates by rhodium(II) (N-dodecylbenzenesulfonyl)prolinate (Rh2(S-DOSP)4, 1) in the presence of dienes results in a direct and highly enantioselective method for the formation of cis-divinylcyclopropanes. Combination of this process with a subsequent Cope rearrangement re...

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Veröffentlicht in:Journal of the American Chemical Society 1998-04, Vol.120 (14), p.3326-3331
Hauptverfasser: Davies, Huw M. L, Stafford, Douglas G, Doan, Brian D, Houser, Jeffrey H
Format: Artikel
Sprache:eng
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Zusammenfassung:Decomposition of vinyldiazoacetates by rhodium(II) (N-dodecylbenzenesulfonyl)prolinate (Rh2(S-DOSP)4, 1) in the presence of dienes results in a direct and highly enantioselective method for the formation of cis-divinylcyclopropanes. Combination of this process with a subsequent Cope rearrangement results in a highly enantioselective synthesis of a variety of cycloheptadienes containing multiple stereogenic centers.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja974201n