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Short Paper | Regular issue | Vol 94, No. 7, 2017, pp.1337-1350
Published online, 29th May, 2017
DOI: 10.3987/COM-17-13725
Catalytic Enantioselective Desymmetrization of meso-Aziridines with Fluoromalonates

Seiya Fukagawa, Yingjie Xu, Masahiro Anada, Tatsuhiko Yoshino, and Shigeki Matsunaga*

*Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan

Abstract

Catalytic enantioselective desymmetrization of meso-aziridines with fluoromalonates is described. Optimization studies revealed that the appropriate combination of Brønsted basic metal and Lewis acidic metal is important for promoting the reaction using fluoromalonates. A heterodinuclear Gd(OiPr)3/Y(OTf)3/Schiff base = 1:1:1 was the best catalyst, and ring-opening adducts, synthetic precursors for α-fluoro-γ-amino acids, were obtained in 98%~17% yield and >99.5%~99% ee. Transformation of the ring-opening adduct into α-fluoro-γ-lactam was also demonstrated.