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Communication | Special issue | Vol 76, No. 2, 2008, pp.995-1000
Published online, 2nd June, 2008
DOI: 10.3987/COM-08-S(N)59
Kinetic Resolution of 1,2-Diols Using Nitrogen-Tethered Bisimidazoline-Copper(I) Catalyzed Benzoylation

Takayoshi Arai,* Tomoe Mizukami, Asami Mishiro, and Akira Yanagisawa

*Department of Chemistry, Graduate School of Science, Chiba University, Inage, Chiba 263-8522, Japan

Abstract

Nitrogen-tethered bisimidazoline (Nb-imidazoline) ligand was utilized in the Cu(I)-catalyzed benzoylation of 1,2-diols. With the assistance of i-Pr2NEt, the reaction of rac-1,2-diols with o-methylbenzoyl chloride was smoothly catalyzed by Nb-imidazoline-CuCl in CH2Cl2 to give the corresponding o-methylbenzoylated secondary alcohols in up to 79% ee.