Synthesis of N-Boc-Propargylic and Allylic Amines by Reaction of Organomagnesium Reagents with N-Boc-Aminals and Their Oxidation to N-Boc-Ketimines
Taichi Kano, Ryohei Kobayashi and Keiji Maruoka*
*Department of Chemistry, Graduate School of Science, Kyoto
University, Sakyo, Kyoto 606-8502, Japan, Email: maruoka
kuchem.kyoto-u.ac.jp
T. Kano, R. Kobayashi, K. Maruoka, Org. Lett., 2016, 18, 276-279.
DOI: 10.1021/acs.orglett.5b03446
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Abstract
The reaction between N-Boc-aminals and organomagnesium reagents provides previously inaccessible N-Boc-protected propargylic and allylic amines via in situ generated N-Boc-imine intermediates. The obtained N-Boc-propargylic amines could be readily converted into unprecedented N-Boc-ketimines by oxidation with manganese dioxide.
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Key Words
propargylic amines, allylic amines, alkylamines
ID: J54-Y2016
