Abstract
Abstract Trans-2,6-disubstituted-4-piperidones were synthesized by [4+2]type cycloaddition of chiral aldimines (5) with 2-silyloxy-1,3-butadiene (3) in the presence of Lewis acids. In the cycloaddition, only two 2,6-trans isomers (chelation and nonchelation products) were observed and no cis compounds were detected regardless of the Lewis acid used. Chelation-controlled products 6b, 8b, and 9b were obtained selectively by the use of TiCl4-i-PrCN and 6a was obtained with high selectivity when TMSOTf or Zn(OTf)2 was used as a Lewis acid at 4°C. The scope of the reaction is also described.
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