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Communication | Regular issue | Vol 32, No. 1, 1991, pp.7-10
Published online, 1st January, 1970
DOI: 10.3987/COM-90-5604
An Enantioselective Construction of Pyrrolidones Bearing Functionalized Appendages via an Asymmetric Intramolecular Michael Reaction

Yoshiro Hirai, Takashi Terada, Hideko Katoh, Sayuri Sonohara, and Takefumi Momose*

*Faculty of Pharmaceutical Sciences, Toyama Medical and Pharmaceutical University, 2630 Sugitani, Toyama, Toyama 930-0194, Japan

Abstract

The intramolecular Michael reaction of acyclic compounds 9 and 10 to form pyrrolidones is reported. Cyclization of 9 and 10 using (R)-(+)-1-phenylethylamine as a mediator gave the pyrrolidones (+)-11 and (+)-12 in 63% and 65% enantiomeric excess, respectively. when (S)-(-)-1-phenylethylamine was used, (-)-11 and (-)-12 were obtained in similar optical yields, respectively.