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Communication | Regular issue | Vol 102, No. 6, 2021, pp.1083-1090
Published online, 30th March, 2021
DOI: 10.3987/COM-21-14433
Acylative Desymmetrization of Glycerol Derivatives by Chiral DMAP Derivatives

Hiroki Mandai,* Kosuke Ashihara, Koichi Mitsudo, and Seiji Suga*

*Department of Pharmacy, Faculty of Pharmacy, Gifu University of Medical Science, 4-3-3 Nijigaoka, Kani, Gifu, 509-0293

Abstract

An efficient enantioselective acylative desymmetrization of glycerol was developed by using a chiral DMAP derivatives 1e having a 1,1ʹ-binaphthyl unit. The reactions required only 0.1 mol% of the catalyst and showed moderate to good enantioselectivity (up to 94:6 er). Control experiments revealed that the first acylation of a glycerol derivative proceeded selectively rather than the second acylation to give diacylate.