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

Authors: Huw M. L. Davies , Douglas G. Stafford , Brian D. Doan , and Jeffrey H. Houser

J. Am. Chem. Soc.,

1998, 120 (14), 3326–3331

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.

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