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Synfacts 2006(12): 1266-1266  
DOI: 10.1055/s-2006-955607
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Stereoselectivity Reversal in Allylation ofN-tert-Butanesulfinyl Imines

Contributor(s): Paul Knochel, Andrei Gavryushin
X.-W. Sun, M.-H. Xu*, G.-Q. Lin*
Shanghai Institute of Organic Chemistry and Shanghai Institute of Materia Medica, P. R. of China
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Publication History

Publication Date:
22 November 2006 (online)

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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.