Highly Efficient, Catalytic Meerwein-Ponndorf-Verley Reduction with a Novel Bidentate Aluminum Catalyst

Takashi Ooi; Tomoya Miura; Keiji Maruoka

doi:10.1002/(SICI)1521-3773(19980918)37:17<2347::AID-ANIE2347>3.0.CO;2-U

Highly Efficient, Catalytic Meerwein-Ponndorf-Verley Reduction with a Novel Bidentate Aluminum Catalyst

Angew Chem Int Ed Engl. 1998 Sep 18;37(17):2347-2349. doi: 10.1002/(SICI)1521-3773(19980918)37:17<2347::AID-ANIE2347>3.0.CO;2-U.

Authors

Takashi Ooi¹, Tomoya Miura¹, Keiji Maruoka¹

Affiliation

¹ Department of Chemistry, Graduate School of Science, Hokkaido University, Sapporo, 060-0810 (Japan), Fax: (+81) 11-746-2557.

Abstract

Double electrophilic activation of carbonyl groups allows a modern variant of the Meerwein-Ponndorf-Verley reduction to be carried out under mild conditions with bidentate catalyst 1 (see reaction). Various carbonyl substrates can be reduced efficiently at room temperature in CH₂ Cl₂ with 2-propanol or sec-phenethyl alcohol in the presence of a catalytic amount of 1. This system is also applicable to the Oppenauer oxidation of secondary alcohols to the corresponding ketones.

Keywords: Aluminum; Asymmetric synthesis; Homogeneous catalysis; Oxidations; Reductions.