Bifunctional Asymmetric Catalysis: Amplification of Brønsted Basicity Can Orthogonally Increase the Reactivity of a Chiral Brønsted Acid
摘要：
The reactivity of a series of symmetrical chiral Brnsted acids (polar ionic hydrogen-bond donors) follows the counterintuitive trend wherein the more Brnsted basic member is a more effective catalyst for the aza-Henry (nitro-Mannich) reaction. This new design element leads to a substantially more reactive catalyst for the aza-Henry reaction, one that can promote the addition of a secondary nitroalkane. Additionally, when an achiral Brnsted acid (TfOH) is used in slight excess of the neutral, chiral bisamidine ligand, diastereoselection can be optimized to levels generally greater than 15:1 while the enantioselection remains unchanged at generally >90% ee.
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DOI：
10.1021/ja908814h
被引量：
年份：
2010
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