Is Reaction Acceleration of Microdroplet Chemistry Favorable to Controlling the Enantioselectivity?

Abstract

Microdroplet chemistry has been proven to amazingly accelerate many chemical and biological reactions in the past 2 decades. Current microdroplet accelerated reactions are predominantly symmetric synthetic but minorly asymmetric synthetic reactions, where stereoselectivity is scarcely concerned. This study selected unimolecular and bimolecular reactions, multicomponent Passerini reactions, and enzymatic ketone reduction as the model reactions to illustrate whether reaction acceleration of microdroplet chemistry is favorable to retaining a chiral center and controlling the enantioselectivity or not. The results illustrated that microdroplet chemistry did not disrupt pre-existing stereogenic centers in chiral starting materials during reactions but did harm to stereospecificity in asymmetric catalysis by chiral catalysts and chiral organic ligands with the exclusion of enzymatic reactions. Our preliminary study reminds us of more cautions to the product enantioselectivity when conducting asymmetric catalysis in microdroplets. We also hope this study may promote more valuable further research on the stereoselectivity of microdroplet chemistry.

Mild Diarylmethylation of Indoles through Regioselective 1,6-Hydroarylation of para-Quinone Methides in Microdroplets/Thin Film

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Recent Applications of Photothermal Conversion in Organic Synthesis

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Stereoselectivity in electrosprayed confined volumes: asymmetric synthesis of warfarin by diamine organocatalysts in microdroplets and thin films

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