Journal of the American Chemical Society, Vol.120, No.14, 3326-3331, 1998
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 (Rh-2(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.
Keywords:RHODIUM-STABILIZED VINYLCARBENOIDS;COPE REARRANGEMENT;CATALYZED DECOMPOSITION;7-MEMBERED CARBOCYCLES;THERMAL REARRANGEMENT;CYCLIZATION REACTIONS;ANNULATION REACTIONS;CONVENIENT SYNTHESIS;3+4 ANNULATION;CYCLO-ADDITION