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Short Paper | Regular issue | Vol 83, No. 11, 2011, pp.2577-2588
Published online, 30th August, 2011
DOI: 10.3987/COM-11-12254
C2-Symmetric Pyrrolidine-Based Chiral Ammonium Salts as a Phase-Transfer Catalyst

Tatsuya Ishikawa, Kazuhiro Nagata, Sachiko Kani, Mamoru Matsuo, Daisuke Sano, Takuya Kanemitsu, Michiko Miyazaki, and Takashi Itoh*

*School of Pharmaceutical Sciences, Showa University, 1-5-8 Hatanodai, Shinagawa-ku, Tokyo 142-8555, Japan

Abstract

Chiral pyrrolidinium salts having substituents at the α, α’ positions were synthesized to develop a chiral phase-transfer catalyst which have more simplified structure. The catalytic function of these synthesized catalysts was evaluated using asymmetric benzylation of N-(diphenylmethylene)glycine tert-butyl ester, and α,α’-disubstituded pyrrolidinium salts having an alkyl chain with a hydroxyl group at a chiral center were found to afford moderate enantioselectivity.