Copper(I) Halide Promoted Diastereoselective Synthesis of Chiral Propargylamines and Chiral Allenes using 2‑Dialkylaminomethylpyrrolidine, Aldehydes, and 1‑Alkynes

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...

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Bibliographic Details
Published in:Journal of organic chemistry 2013-02, Vol.78 (4), p.1463-1470
Main Authors: Gurubrahamam, Ramani, Periasamy, Mariappan
Format: Article
Language:English
Subjects:
Aldehydes - chemistry
Alkadienes - chemistry
Alkynes - chemistry
Copper - chemistry
Hydrocarbons, Halogenated - chemistry
Molecular Structure
Pargyline - analogs & derivatives
Pargyline - chemical synthesis
Pargyline - chemistry
Propylamines - chemical synthesis
Propylamines - chemistry
Pyrrolidines - chemistry
Stereoisomerism
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo302534f