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

作者信息

Kuo Shen-Chun, Chen Frank, Hou Donald, Kim-Meade Agnes, Bernard Charles, Liu Jinchu, Levy Stacy, Wu George G

机构信息

Chemical Process Research and Development, Schering-Plough Research Institute, 1011 Morris Avenue, Union, NJ 07083, USA.

出版信息

J Org Chem. 2003 Jun 13;68(12):4984-7. doi: 10.1021/jo034380t.

DOI:10.1021/jo034380t

PMID:12790617

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 applied to the synthesis of a promising anticancer agent.

摘要