Asymmetric synthesis of the methyl and benzyl ethers of erythro-. alpha.,. beta.-diphenyl-. beta.-hydroxyethanol and erythro-. alpha.,. beta.-diphenyl-. beta.- …

…, MS Haque, RM Przeslawski

Index: Davis, Franklin A.; Haque, M. S.; Przeslawski, Robert M. Journal of Organic Chemistry, 1989 , vol. 54, # 8 p. 2021 - 2024

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Citation Number: 49

Abstract

Our synthetic strategy is outlined in Scheme I and begins with the preparation of enantiomerically pure (+)-(SI-benzoin (2). This compound can be prepared in> 96% optical purity and 84% isolated yield by oxidation of the sodium enolate of deoxybenzoin (1) with (+)- (2R, 8aS)-(camphorylsulfony1) oxaziridine (5). 2 On a small scale (0.5 mmol)(+)-2 is separated from the sulfonimine 6 byproduct by preparative TLC or flash chromatography. ...