(1) The catalytic enantioselective fluorination of N-H-free 3-substituted oxindoles was accomplished by Sc(III)/N,N'-dioxide complex. Under mild reaction conditions, a series of 3-aryl- and 3-alkyl-3-fluoro-2-oxindoles were obtained in excellent yields (up to 98%) and enantioselectivities (up to 99% ee) by using N-fluorobisbenzenesulphonimide (NFSI) as the fluorination agent. MaxiPost was synthesized efficiently in 81% yield with 96% ee. (2) The asymmetric ring-opening of meso-aziridines with primary alcohols is realized using a N,N'-dioxide–Mg(OTf)2 complex as the catalyst. The desired vicinal trans-β-amino ethers are afforded in good yields and enantioselectivities. Aniline and water could also be used as the nucleophiles for the ring-opening under the identical catalyst system. Keywords: asymmetric fluorination; oxindoles, MaxiPost; ring-opening of meso-aziridines; primary alcohols; aniline; water. References [1]J. Li, Y. F. Cai, W. L. Chen, X. H. Liu, L. L. Lin, X. M. Feng, J. Org. Chem., 2012, 77, 9148. [2]J. Li, Y. T. Liao, Y. L. Zhang, X. H. Liu, L. L. Lin, X. M. Feng, Chem. Commun., 2014, 50, 6672.

Catalytic, asymmetric fluorination of oxindoles and ring-opening of meso-aziridines with primary alcohols

251st National Meeting (2016)

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