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Enantioselective Nucleophilic Addition of Trimethylsilylacetylene to N -Phosphinoylimines Promoted by C 2 -Symmetric Proline-Derived β-Amino Alcohol

✍ Scribed by Zhu, Shaoqun; Yan, Wenjin; Mao, Bin; Jiang, Xianxing; Wang, Rui

Book ID
126310167
Publisher
American Chemical Society
Year
2009
Tongue
English
Weight
874 KB
Volume
74
Category
Article
ISSN
0022-3263

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## Abstract A new synthetic methodology for the preparation of optically active propargylamines is described. The alkynylation of aromatic, heteroaromatic, aliphatic and α,β‐unsaturated __N__‐(diphenylphosphinoyl)imines was investigated by using diethylzinc and a proline‐derived β‐amino alcohol. __

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A (+)-3-carene derived aminoalcohol was successfully used as a chiral ligand in the catalytic enantioselective diethylzinc addition to various aldehydes. Very high enantiomeric excess (up 98% in 1-(2-methoxyphenyl)-1-propanol) was obtained. A plausible mechanism has been suggested for the observed e