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Synthesis of Enantiomerically Pure α-Substituted Propargylic Amines by Reaction of Organoaluminum Reagents with Oxazolidines

Various oxazolidines prepared in two steps from (R)-phenylglycinol react at 0 °C with dialkylalkynylalane−triethylamine complexes in the presence of trimethylaluminum in high yield and diastereoselectivity. Enantiomerically pure primary α-substituted propargylamines can be easily obtained in two ste...

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Bibliographic Details
Published in:Journal of organic chemistry 2000-10, Vol.65 (20), p.6423-6426
Main Authors: Blanchet, J, Bonin, M, Micouin, L, Husson, H.-P
Format: Article
Language:English
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Summary:Various oxazolidines prepared in two steps from (R)-phenylglycinol react at 0 °C with dialkylalkynylalane−triethylamine complexes in the presence of trimethylaluminum in high yield and diastereoselectivity. Enantiomerically pure primary α-substituted propargylamines can be easily obtained in two steps after removal of ferrocenylmethyl protective group under smooth acidic conditions and oxidative cleavage of the chiral appendage.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo0003706