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Pure Appl. Chem., 2006, Vol. 78, No. 2, pp. 267-274

Catalytic asymmetric addition reactions leading to carbon-carbon bond formation: Phenyl and alkenyl transfer to aldehydes and alkynylation of α-imino esters

Jian-Xin Ji, Jing Wu, Lijin Xu, Chiu-Wing Yip, Kim Hung Lam and Albert S. C. Chan

Department of Applied Biology and Chemical Technology, Hong Kong Polytechnic University, Hong Kong, China

Abstract: Optically active tertiary aminonaphthol ligands were obtained by a new, convenient procedure and were found to catalyze the enantioselective alkenyl and phenyl transfer to aldehydes in high yields and excellent enantiomeric excesses (ee's). The catalytic asymmetric introduction of alkynyl functionality to α-amino acid derivatives was realized by the direct addition of terminal alkynes to α-imino ester in the presence of chiral copper(I) complex under mild reaction conditions.