Role of Pseudoephedrine as Chiral Auxiliary in the “Acetate-Type” Aldol Reaction with Chiral Aldehydes; Asymmetric Synthesis of Highly Functionalized Chiral …

…, L Carrillo, JL Vicario, D Badía, E Reyes

Index: Reyes, Efraim; Vicario, Jose L.; Carrillo, Luisa; Badia, Dolores; Uria, Uxue; Iza, Ainara Journal of Organic Chemistry, 2006 , vol. 71, # 20 p. 7763 - 7772

Full Text: HTML

Citation Number: 11

Abstract

We have studied in depth the aldol reaction between acetamide enolates and chiral α- heterosubstituted aldehydes using pseudoephedrine as chiral auxiliary under double stereodifferentiation conditions, showing that high diastereoselectivities can only be achieved under the matched combination of reagents and provided that the α-heteroatom- containing substituent of the chiral aldehyde is conveniently protected. Moreover, the ...