Organic Chemistry Portal



Cp2TiCl-Mediated Selective Reduction of α,β-Epoxy Ketones

Christophe Hardouin, Floris Chevallier, Bernard Rousseau and Eric Doris

*CEA/Saclay, Service des Molécules Marquées, Bât. 547, Département de Biologie Cellulaire et Moléculaire, 91191 Gif sur Yvette Cedex, France, Email:

C. Hardouin, F. Chevallier, B. Rousseau, E. Doris, J. Org. Chem., 2001, 66, 1046-1048.

DOI: 10.1021/jo001358g

see article for more reactions


Low-valent Cp2TiCl selectively reduces selected α,β-epoxy ketones to the corresponding aldol products under mild conditions. A chiral epoxide was converted without any loss of optical purity. The addition of collidine hydrochloride enables a system catalytic in titanocene.

see article for more examples

proposed mechanism

Key Words

reduction of epoxides, β-hydroxy ketones, low-valent titanium

ID: J42-Y2001