Bifunctional catalysis is a widely used method as to the stereoselective synthesis building C-C bond, including the commonly applied Michael addition. Such method has good compatibility, high activity under mild conditions. Recent research went throught several ways of catalyzed asymmetric nitro-Michael addition. A major downside to the majority of these methods is the low reaction efficiency, employing high catalytic loading and long reaction time. Rearding C-C bond construction, aminoboronic acid-based organocatalysis has been the focus of our group recently.  Herein a proline-based aminoboronic acid bifunctional catalyst has been prepared by a multi-step synthesis as a novel and efficient methodology towards asymmetric nitro-Michael addition. The catalyst showed broad substrate tolerance, high level of conversion and optical purity within a minimum loading and time consumption. Such B-N bifunctional catalytic system suggests an effective catalytic strategy towards the asymmetric synthesis.

Organoboron bifunctional catalysis of asymmetric nitro-Michael addition

2019 Fall National Meeting

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