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Synthesis of Allylic Amines by Asymmetric Transfer Hydrogenation of α,β-Unsaturated N-(tert-Butylsulfinyl)imines

Elisabet Selva, Yeshua Sempere, Débora Ruiz-Martínez, Óscar Pablo and David Guijarro*

*Departamento de Química Orgánica, Facultad de Ciencias and Instituto de Síntesis Orgánica (ISO), Universidad de Alicante, Apdo. 99, 03080 Alicante, Spain, Email: dguijarroua.es

E. Selva, Y. Sempere, D. Ruiz-Martínez, O. Pablo, D. Guijarro, J. Org. Chem., 2017, 82, 13693-13699.

DOI: 10.1021/acs.joc.7b02472 (free Supporting Information)


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Abstract

Transfer hydrogenation of chiral α,β-unsaturated N-(tert-butylsulfinyl)ketimines followed by removal of the sulfinyl group provides primary allylic amines with enantiomeric excesses from 97 to >99%.

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Key Words

reduction of imines, isopropanol, allylic amines, ATH, N-sulfinylimines, ruthenium catalyst


ID: J42-Y2017