Synthesis of enantiomerically pure alpha-substituted propargylic amines byreaction of organoaluminum reagents with oxazolidines

Authors
Blanchet, J Bonin, M Micouin, L Husson, HP
Citation
J. Blanchet et al., Synthesis of enantiomerically pure alpha-substituted propargylic amines byreaction of organoaluminum reagents with oxazolidines, J ORG CHEM, 65(20), 2000, pp. 6423-6426
Citations number
31
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
65
Issue
20
Year of publication
2000
Pages
6423 - 6426
Database
ISI
SICI code
0022-3263(20001006)65:20<6423:SOEPAP>2.0.ZU;2-5
Abstract
Various oxazolidines prepared in two steps from (R)-phenylglycinol react at 0 degrees C with dialkyl-alkynylalane-triethylamine complexes in the prese nce of trimethylaluminum in high yield and diastereoselectivity. Enantiomer ically pure primary alpha-substituted propargylamines cah be easily obtaine d in two steps after removal of ferrocenylmethyl protective group under smo oth acidic conditions and oxidative cleavage of the chiral appendage.