Enantioselective synthesis of α-tertiary hydroxyaldehydes by palladium-catalyzed asymmetric allylic alkylation of enolates

BM Trost, J Xu, M Reichle

Index: Trost, Barry M.; Xu, Jiayi; Reichle, Markus Journal of the American Chemical Society, 2007 , vol. 129, # 2 p. 282 - 283

Full Text: HTML

Citation Number: 79

Abstract

Chiral α-tertiary hydroxyaldehydes are very versatile building blocks in synthetic chemistry. Herein, we report the first examples of a catalytic asymmetric protocol for the synthesis of such compounds from readily available α-halo or α-hydroxy ketones or enol silyl ethers with excellent yields and enantioselectivity. Its synthetic utility is demonstrated in the short, efficient formal synthesis of (S)-oxybutynin. In this process, the chiral ligand controls the ...