Stereoselectivity Reversal in Allylation ofN-tert-Butanesulfinyl Imines

Significance

Chiral homoallylic amines are important precusors for a variety of organic compounds. Diastereoselective allylation of imines bearing chiral auxiliaries is one of the best methods for their synthesis. The authors reported here an interesting approach to the synthesis of both enantiomers of various chiral homoallylic amines using a single enantiomer of N-tert-butanesulfinyl imine as a chiral auxiliary. By a simple switch of the reaction conditions the diastereoselectivity of the reaction can be totally reversed, in both cases achieving 92-98%. Besides, the reaction conditions, which allow the allylation of substituted aceto­phenone imines with very good diastereoselectivities, were found.