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A Bench-Stable Homodinuclear Ni2-Schiff Base Complex for Catalytic Asymmetric Synthesis of α-Tetrasubstituted anti-α,β-Diamino Acid Surrogates

Zhihua Chen, Hiroyuki Morimoto, Shigeki Matsunaga* and Masakatsu Shibasaki*

*Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan, Email: mshibasamol.f.u-tokyo.ac.jp, smatsunamol.f.u-tokyo.ac.jp

Z. Chen, H. Morimoto, S. Matsunaga, M. Shibasaki, J. Am. Chem. Soc., 2008, 130, 2170-2171.

DOI: 10.1021/ja710398q (free Supporting Information)



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Abstract

Catalytic asymmetric direct Mannich-type reactions of α-substituted nitroacetates using a new bench-stable homodinuclear Ni2-Schiff base complex gave Mannich products in high ee, that serve as precursors for anti-α,β-diamino acids with an α-tetrasubstituted carbon stereocenter. The Ni complex was also applicable to direct Mannich-type reactions of malonates and β-keto ester.

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Key Words

β-amino acids, active methylenes


ID: J48-Y2008-0430