title: Copper(I) halide promoted diastereoselective synthesis of chiral propargylamines and chiral allenes using 2-dialkylaminomethylpyrrolidine, aldehydes, and 1-alkynes.
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.
authors: School of Chemistry, University of Hyderabad, Central University P.O., Hyderabad 500046, India.
authors: Ramani
authors: R
authors: Gurubrahamam
authors: Mariappan
authors: M
authors: Periasamy
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000466:Alkadienes / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry*; D003300:Copper / Q000737:chemistry*; D006846:Hydrocarbons, Halogenated / Q000737:chemistry*; D015394:Molecular Structure; D010293:Pargyline / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D011437:Propylamines / Q000138:chemical synthesis* / Q000737:chemistry*; D011759:Pyrrolidines / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D000466:Alkadienes; D000480:Alkynes; D006846:Hydrocarbons, Halogenated; D011437:Propylamines; D011759:Pyrrolidines; C009054:propargylamine; D003300:Copper; D010293:Pargyline