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  • Title: Copper(I) halide promoted diastereoselective synthesis of chiral propargylamines and chiral allenes using 2-dialkylaminomethylpyrrolidine, aldehydes, and 1-alkynes.
    Author: Gurubrahamam R, Periasamy M.
    Journal: J Org Chem; 2013 Feb 15; 78(4):1463-70. PubMed ID: 23320792.
    Abstract:
    Copper bromide promoted reactions of aldehydes, 1-alkynes, and chiral 2-dialkylaminomethylpyrrolidine at 25 °C give the corresponding chiral propargylamine derivatives in up to 96% yield and 99:1 dr that are readily converted to the corresponding disubstitued chiral allenes in up to 81% yield and 99% ee upon reaction with CuI in dioxane at 100 °C.
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