Tetrahedron: Asymmetry

Synthesis of highly enantiomerically enriched amines by the diastereoselective addition of triorganozincates to N-(tert-butanesulfinyl) imines

R Almansa, D Guijarro, M Yus

Index: Almansa, Raquel; Guijarro, David; Yus, Miguel Tetrahedron Asymmetry, 2008 , vol. 19, # 21 p. 2484 - 2491

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Citation Number: 37

Abstract

The reaction of triorganozincates with (R)-N-(tert-butanesulfinyl) imines gives the expected α- branched sulfinamides in good to excellent yields with diastereomeric ratios of up to 98: 2. The N-sulfinyl group of the products can be easily removed by acidic treatment, affording the corresponding chiral primary amines in enantiomeric excesses of up to 96%. The reactivity and the selectivity shown by the triorganozincates are different from the ones observed ...