Published TCIMAIL newest issue No.197
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A Sn(OTf)2-Mediated Diastereoselective Vinylogous Mannich-Type Reaction of Chiral Imines
Yang et al. have reported a stereoselective synthesis of chiral 6-substituted piperidinones and 2-substituted piperidines via Sn(OTf)2-mediated diastereoselective vinylogous Mannich-type reaction. The reaction began with the condensation of chiral 1-(1-naphthyl)ethylamine with aldehydes. The in situ-generated chiral imines were then treated with the silyl ketene acetal in the presence of Sn(OTf)2 to give the chiral adducts. Using aldehydes bearing steric bulky residues gave good diastereoselectivities as high as 9:1. The chiral adducts provided the chiral piperidinones and piperidines. Furthermore, they have applied the strategy to a synthesis of (S)-anabasine, which is a tobacco alkaloid.
