Orthoacylimines: A new class of chiral auxiliaries for nucleophilic addition of organolithium reagents to imines

…, G Solberghe, C Lauzon, AB Charette

Index: Boezio, Alessandro A.; Solberghe, Geoffrey; Lauzon, Caroline; Charette, Andre B. Journal of Organic Chemistry, 2003 , vol. 68, # 8 p. 3241 - 3245

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Citation Number: 21

Abstract

A new class of orthoacylimine-derived chiral auxiliaries has been synthesized and tested in the nucleophilic addition of organolithium reagents to imines. The precursors can be prepared by an aza-Wittig reaction between the corresponding orthoacyl azide and a variety of aldehydes in the presence of trialkylphosphines. The nucleophilic addition of organolithium reagents led to the addition products in good yields and with good to ...