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Synfacts 2009(10): 1157-1157  
DOI: 10.1055/s-0029-1218015
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Enantioselective Synthesis of syn-α,β-Diamino Acid Derivatives

Contributor(s): Benjamin List, Ilija Èorić
L. Li, M. Ganesh, D. Seidel*
The State University of New Jersey, piscataway, USA
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Publication History

Publication Date:
22 September 2009 (online)

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Significance

A catalytic enantioselective ­Mannich reaction of α-isothiocyanato imide (2) with sulfonyl-protected imines 3 has been reported. Using quinidine-derived catalyst 1, syn-α,β-­diamino acid derivatives 4 were obtained in high yields and with high diastereoselectivity and enantioselectivity. When 4-nitrophenylsulfonyl (Ns) protected imines that decrease product inhibition by giving less soluble products 4b were used, catalyst loadings of 0.25 mol% were still highly efficient.