N-Boc-aminals as easily accessible precursors for less accessible N-Boc-imines: facile synthesis of optically active propargylamine derivatives using Mannich-type reactions

Research paper by Taiga Yurino, Yusuke Aota, Daisuke Asakawa, Taichi Kano, Keiji Maruoka

Indexed on: 29 Mar '16Published on: 26 Mar '16Published in: Tetrahedron


We developed a facile and practical synthesis of N-Boc-aminals, which can be used as precursors for less accessible N-Boc-imines. Aminals were obtained via simple dehydration condensation reactions of t-butyl carbamate (BocNH2) and various aldehydes in acetic anhydride, followed by filtration and washing with hexane. The obtained N-Boc-alkynylaminals could be successfully applied in enantioselective Mannich-type reactions, catalyzed by chiral phosphoric acids, to afford optically active propargylamine derivatives.

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