A Nanovessel-Catalyzed Three-Component Aza-Darzens Reaction

Stephen M. Bierschenk,Robert G. Bergman, Kenneth N. Raymond,F. Dean Toste

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY(2020)

Cited 32|Views35
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Abstract
It has been previously demonstrated that nanovessels can be highly competent catalysts providing high rate accelerations and unique selectivity to the organic transformations which they mediate. However, for supramolecular assemblies to be considered a standard reagent in organic synthesis they must first demonstrate the ability to catalyze increasingly complex transformations. Herein, we report a three-component Aza-Darzens reaction that generates N-phenylaziridines, catalyzed by a supramolecular host, that provides the stereoisomer opposite to the one generated in bulk solution (trans vs cis). This transformation constitutes a rare catalytic three-component coupling within a supramolecular assembly, providing a supramolecular solution to a synthetically challenging transformation.
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