The Journal of organic chemistry

Catalytic Asymmetric α-Alkylation of Ketones and Aldehydes with N-Benzylic Sulfonamides through Carbon–Nitrogen Bond Cleavage

ZT Weng, Y Li, SK Tian

Index: Weng, Zhen-Tao; Li, Yuan; Tian, Shi-Kai Journal of Organic Chemistry, 2011 , vol. 76, # 19 p. 8095 - 8099

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Citation Number: 35

Abstract

A range of ketones and aldehydes smoothly undergo asymmetric SN1 α-alkylation with N- benzylic sulfonamides in the presence of 10 mol% of a chiral imidazolidinone and trifluoroacetic acid to give the corresponding products in good to excellent yields and with good enantioselectivity. This chemistry has been successfully extended to the asymmetric desymmetrization of 4-substituted cyclohexanones, which exhibits greater than 99: 1 ...