Base-Induced Coupling of α-Azido Ketones with Aldehydes − An Easy and Efficient Route to Trifunctionalized Synthons 2-Azido-3-hydroxy Ketones, 2-Acylaziridines, and 2-Acylspiroaziridines

Abstract

An improved synthesis of α-azido ketones under phase-transfer conditions has been developed. The transformation of α-azido ketones into acyclic and heterocyclic 2-azido-3-hydroxy ketones has been demonstrated and the relative configurations of the chromanone derivatives have been determined by X-ray analysis. Treatment of the aldol-type products with triphenylphosphane afforded 2-acylaziridines and the hitherto unknown spiro[chroman-3,2′-aziridin]-4-ones. The relative configuration of the spiroaziridines was determined by NOE measurements.