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Communication | Special issue | Vol 66, No. 1, 2005, pp.81-86
Published online, 11th October, 2005
DOI: 10.3987/COM-05-S(K)26
Asymmetric Introduction of Nucleophiles to the 2-Position of Pyrrolidine Ring through N-Acylpyrrolidinium Ion

Osamu Onomura, Takashi Ikeda, and Yoshihiro Matsumura*

*Department of Pharmaceutical Sciences, Graduate School of Biomedical Sciences, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki 852-8521, Japan

Abstract

Asymmetric carbon-carbon bond-forming reaction at the 2-position of a pyrrolidine ring was achieved. The reaction involved a chiral Ti(IV) catalyzed coupling between 1-methoxycarboyl-2-methoxypyrrolidine and silyl enol ethers to afford 2-substituted pyrrolidines with up to 53 % ee.