Organic Chemistry Portal



Phase-transfer-catalyzed asymmetric Darzens reaction

Shigeru Arai*, Yoshiki Shirai, Toshimasa Ishida and Takayuki Shioiri

*Graduate School of Pharmaceutical Sciences, Chiba University, 1-33 Yayoi-Cho, Inage-ku, Chiba 263-8522, Japan, Email:

S. Arai, Y. Shirai, T. Ishida, T. Shioiri, Tetrahedron, 1999, 55, 6375-6386.

DOI: 10.1016/S0040-4020(99)00213-6

see article for more reactions


Catalytic asymmetric Darzens reactions of α-chloro acyclic and cyclic ketones promoted by a chiral phase-transfer catalyst derived from cinchonine gave the desired α,β-epoxy ketones with moderate to high enantiomeric excesses under mild reaction conditions.

see article for more examples

Key Words

Epoxides, Darzens Condensation, Asymmetric Catalyst, Phase Transfer, Organocatalysis

ID: J72-Y1999-450