Highly Efficient and Stereoselective Mukaiyama Aldol Reaction with Chiral Aziridine‐2‐carboxaldehyde and Its Synthetic Applications

Asian Journal of Organic Chemistry
2022.0

Abstract

A straightforward and highly diastereoselective synthesis of beta-(aziridin-2-yl)-beta-hydroxy ketones was achieved by the Mukaiyama aldol reaction of optically pure 1-(alpha-methylbenzyl)-aziridine-2-carboxaldehyde and various enol-silanes in ZnCl2 via a chelation-controlled transition state (98 : 2 dr and >82% yields). These beta-(aziridin-2-yl)-beta-hydroxy ketones were applied for the synthesis of various alkaloids including epiallo-isomuscarine, epi-enigmol, and epi-galantinic acid.

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