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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
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Section:Abstract
Catalytic asymmetric direct Mannich-type reactions of α-substituted nitroacetates using a new bench-stable homodinuclear Ni2−Schiff base 1b complex are described. The Ni2−1b complex gave Mannich products, precursors for anti-α,β-diamino acids with an α-tetrasubstituted carbon stereocenter, in >99−91% ee. The Ni2−1b complex was also applicable to direct Mannich-type reactions of malonates and β-keto ester, giving products in high stereoselectivity (up to 99% ee, dr >97:3). Preliminary mechanistic studies suggested that the dinuclear Ni metal centers had key roles to achieve good reactivity and high stereoselectivity.
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This article has been cited by 42 ACS Journal articles (5 most recent appear below).
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History
- Published In Issue February 20, 2008
- Received November 27, 2007
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