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Synfacts 2005(3): 0331-0331  
DOI: 10.1055/s-2005-921626
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Stereoselective Reductive Coupling of Chiral Sulfinyl Imines with Aldehydes

Contributor(s): Paul Knochel, Andrei Gavryushin
Y.-W. Zhong, Y.-Z. Dong, K. Fang, K. Izumi, M.-H. Xu*, G.-Q. Lin*
Shanghai Institute of Materia Medica, P. R. of China
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Publikationsverlauf

Publikationsdatum:
22. November 2005 (online)

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Significance

A reductive cross-coupling reaction between aliphatic aldehydes and chiral N-tert-butanesulfinimines in the presence of SmI2 leads to the formation of β-amino alcohols with excellent enantiomeric and diastereomeric excesses and good yields. The products can be used as chiral ligands or auxiliaries in asymmetric synthesis. The method allows also the preparation of important natural compounds like statine, a structural moiety of novel protease blockers, very perspective for pharmacology.