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Paper | Special issue | Vol 95, No. 1, 2017, pp.277-289
Published online, 3rd October, 2016
DOI: 10.3987/COM-16-S(S)17
Kinetic Resolution of Racemic 2-Hydroxyacetals by Asymmetric Esterification Using a Mixed Anhydride Protocol

Kenya Nakata,* Eri Tokumaru, Takahiro Saitoh, Takayoshi Nakahara, Keisuke Ono, Takatsugu Murata, and Isamu Shiina*

*Department of Applied Chemistry, Faculty of Science, Tokyo University of Science, 1-3 Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan

Abstract

The non-enzymatic kinetic resolution of racemic 2-hydroxyacetals via asymmetric esterification with diphenylacetic acid and pivalic anhydride catalyzed by the chiral acyl transfer catalyst (R)-BTM is reported. The reaction transition states were elucidated using theoretical calculations; it was found that 1,3-dioxolane is a suitable reagent for attaining high selectivity.