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Synfacts 2006(3): 0246-0246  
DOI: 10.1055/s-2006-931955
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Aza-Mannich Reactions of Sulfinimines

Contributor(s): Mark Lautens, Josephine Yuen
J. C. Lanter*, H. Chen, X. Zhang, Z. Sui
Johnson & Johnson Pharmaceutical Research and Development, RAritan, USA
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Publikationsdatum:
21. Februar 2006 (online)

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Significance

Addition of enantiomerically pure sulfinimine anions to N-sulfonyl aldimines gave the addition product with excellent diastereoselectivity. The E-sulfonylimine is much more reactive than the Z-sulfonylimine, possibly due to the increased steric hinderance in the transition state of the Z-sulfonylimine. The single diastereoisomer obtained can be rationalized by the steric bulk and orientation of the tert-butylsulfonyl group.