Tetrahedron

Enantioselective synthesis of a chiral fluoropiperidine via asymmetric hydrogenation of a vinyl fluoride

…, JV Mitten, PG Dormer, D Mowrey, F Machrouhi, Y Sun…

Index: Krska, Shane W.; Mitten, Jeffrey V.; Dormer, Peter G.; Mowrey, Dale; Machrouhi, Fouzia; Sun, Yongkui; Nelson, Todd D. Tetrahedron, 2009 , vol. 65, # 44 p. 8987 - 8994

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Citation Number: 16

Abstract

Asymmetric hydrogenation of a vinyl fluoride derivative gives efficient access to enantioenriched 1, 3, 4-trisubstituted piperidine 1 with a stereogenic alkyl fluoride center. Extensive catalyst screening across transition metals and chiral ligands identified only one catalyst, a Rh/Walphos complex, that gives high conversion, enantioselectivity and chemoselectivity for olefin reduction over defluorination. The presence of acid additives in ...

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