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Paper | Special issue | Vol 42, No. 1, 1996, pp.423-435
Published online, 1st January, 1970
DOI: 10.3987/COM-95-S67
Enantioselective [2,3]-Wittig Rearrangement via a Chiral Boron Ester Enolate

Katsuhiko Fujimoto, Chiho Matsuhashi, and Takeshi Nakai

*Department of Chemical Technology, Faculty of Engineering, Tokyo Institute of Technology, Meguro-ku, Tokyo 152, Japan

Abstract

The first enantioselective [2,3]-Wittig rearrangement of α-(allyloxy)- acetates is described which involves a chiral boron enolate with a chiral bis-sulfonamide ligand to afford the α-hydroxy-β-alkyl-γ,δ-unsaturated esters in a high enantioselectivity (>95%ee), along with a high threo diastereoselectivity.