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Pure Appl. Chem., 2012, Vol. 84, No. 7, pp. 1575-1585

Published online 2012-03-13

Designer chiral phase-transfer catalysts for green sustainable chemistry

Keiji Maruoka

Department of Chemistry, Graduate School of Science, Kyoto University, Kyoto 606-8502, Japan

Abstract: A series of chiral quaternary ammonium salts derived from commercially available (R)- or (S)-binaphthol have been designed as new C2-symmetric chiral phase-transfer catalysts. In order to realize the flexible design of these phase-transfer catalysts, the combinatorial design approach has been developed. Chiral high-performance organocatalysts, thus obtained, have been successfully applied to the highly practical asymmetric synthesis of various amino acid derivatives, including α-alkyl and α,α-dialkyl-α-amino acids in addition to alkaloids. Furthermore, several chiral bifunctional phase-transfer catalysts have been designed and synthesized for effecting base-free phase-transfer reactions under essentially neutral conditions in order to realize green sustainable chemistry.