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Chem Commun (Camb). 2013 Oct 3;49(86):10175-7. doi: 10.1039/c3cc45118f.

An easily removable stereo-dictating group for enantioselective synthesis of propargylic amines.

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  • 1Shanghai Key Laboratory of Green Chemistry and Chemical Process, Department of Chemistry East, China Normal University, 3663 North Zhongshan Road, Shanghai 200062, P. R. China. masm@sioc.ac.cn.


We report herein a CuBr-catalyzed three-component coupling of 2-methylbut-3-yn-2-ol, aldehydes and pyrrolidine or 1,2,3,4-tetrahydroisoquinoline leading to the corresponding chiral propargylamines in excellent enantiomeric excess (91 to >99% ee) and high yields (79-95% yield). The dimethylcarbinol unit in 2-methylbut-3-yn-2-ol, which may be easily removed at the later stage to regenerate a terminal alkyne unit for further elaboration, plays a very important role in ensuring high enantioselectivity. This protocol provides easy and very general access to different terminal and non-terminal tertiary propargylic amines.

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