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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: eric.doriscea.fr

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

DOI: 10.1021/jo001358g (free Supporting Information)


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Abstract

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.

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proposed mechanism



Key Words

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


ID: J42-Y2001