The combination of organocatalysis with metal Lewis acid catalysis is an emerging field in chemical catalysis. This new area holds huge potential for the discovery of new carbon-carbon and carbon-heteroatom bond-forming reactions. There is a major challenge hindering the growth of this area, which is the acid-base quenching reaction resulting in catalyst inactivation. In this talk, I will present two strategies developed in our laboratory to synergistically incorporate enamine catalysis with hard metal Lewis acid catalysis. The first strategy is to use competition coordination to solve the critical acid-base quenching problem; the second strategy is to use the inversion of soft/hard approach to solve the acid-base quenching problem. Using these two strategies, we have developed a number of new asymmetric reactions including inverse-electron-demand asymmetric oxo-Diels-Alder reaction of ketones and multicomponent aza-Diels-Alder reaction of ketones. In addition, a new class of chiral bimetallic Lewis acid catalysts will be introduced. An asymmetric ring-opening reaction and a [3+2] cycloaddition reaction of cyclopropanes using these chiral bimetallic catalysts will be presented.

Merging enamine catalysis with hard metal Lewis acid catalysis for asymmetric organic transformation

ACS Fall 2020 Virtual Meeting

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