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Asymmetric Induction Reactions. I. Asymmetric Sigmatropic Rearrangements of Sulfur Ylides Derived from Chiral Ketenimines and Trimethylsulfonium Ylide
Hiroi, Kunio,Sato, Shuko
, p. 2331 - 2338 (2007/10/02)
The asymmetric (2,3) sigmatropic rearrangements of 2-alkylamino-3-phenyl-2-pentenyl-methylsulfonium methylides were accomplished by the reaction of ethylphenylketenimines 3 having a chiral carbon next to the nitrogen atom with trimethylsulfonium ylide, and acidic hydrolysis of the imines 4 thus obtained led to optically active 3-methylthiomethyl-3-phenyl-2-pentanone (5).The reaction of ethylphenylketene (-)-menthylimine (3g) with trimethylsulfonium ylide at -78 deg C resulted in the highest optical yield of (R)-(-)-5 in the above sequence.Keywords--asymmetric induction; (2,3) sigmatropic rearrangement; chiral ketenimine; sulfur ylide; trimethylsulfonium ylide
