A novel enantioselective alkylation and its application to the synthesis of an anticancer agent

…, A Kim-Meade, C Bernard, J Liu, S Levy…

Index: Kuo, Shen-Chun; Chen, Frank; Hou, Donald; Kim-Meade, Agnes; Bernard, Charles; Liu, Jinchu; Levy, Stacy; Wu, George G. Journal of Organic Chemistry, 2003 , vol. 68, # 12 p. 4984 - 4987

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Citation Number: 17

Abstract

A novel enantioselective alkylation of double benzylic substrates with secondary electrophiles is reported. A simple norephedrine-based chiral ligand was synthesized that gives alkylation product in 95% yield and 95% ee. A unique water effect on the enantioselectivity was unveiled. Good to excellent ee values were obtained with a number of double benzylic substrates and secondary electrophiles. This novel reaction has been ...