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A Convenient Synthesis of γ-Amino-Ynamides via Additions of Lithiated Ynamides to Aryl Imines; Observation of an Aza-Meyer-Schuster Rearrangement

Rui Qi, Xiao-Na Wang, Kyle A. DeKorver*, Yu Tang*, Chao-Chao Wang, Qian Li, Hui Li, Ming-Can Lv, Qing Yu, Richard P. Hsung*

*Tianjin University, Tianjin 300072, P. R. of China, University of Wisconsin-Madison, Madison, WI 53705, USA, Dow AgroSciences LLC, 9330 Zionsville Road, Indianapolis, IN 46268, USA, Email: tangyu114gmail.com, rhsungwisc.edu, kadekorverdow.com

R. Qi, X.-N. Wang, K. A. DeKorver, Y. Tang, C.-C. Wang, Q. Li, H. Li, M.-C. Lv, Q. Yu, R. P. Hsung, Synthesis, 2013, 45, 1749-1758.

DOI: 10.1055/s-0033-1338476


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Abstract

An expeditious and convenient method gives γ-amino-ynamides via nucleophilic addition of lithiated ynamides to aryl imines. This work also features an aza-variant of a Meyer-Schuster rearrangement of γ-amino-ynamides and their synthetic utility in intramolecular ketenimine [2+2] cycloadditions.

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Key Words

lithiated ynamides,γ-amino-ynamides, propargyl amines, aryl imines, azetene, aza-Meyer-Schuster rearrangement


ID: J66-Y2013