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  • Title: Unexpected E-stereoselective reductive A3-coupling reaction of terminal alkynes with aldehydes and amines.
    Author: Fan W, Yuan W, Ma S.
    Journal: Nat Commun; 2014 May 22; 5():3884. PubMed ID: 24848772.
    Abstract:
    The transition-metal catalysed three-component coupling of an alkyne, an aldehyde and an amine has been became a widely used method for preparing propargylic amines. Here, we report an unexpected copper(I)-catalysed E-stereoselective reduction of propargylic amines in situ formed from readily available terminal alkynes, aldehydes and 3-pyrroline or isoindoline via [1,5]-hydride transfer, affording E-allylic amines. Through mechanistic studies, it is believed that the unsaturated cyclic dialkylamine is acting as hydrogen donor.
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