期刊
TETRAHEDRON
卷 60, 期 20, 页码 4399-4412出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2004.01.101
关键词
atropisomeric amides; imidazolines; oxazolidines; ephedrine
Condensation of atropisomeric tertiary 2-formyl naphthamides or 2-formyl benzamides with some chiral diamines and amino alcohols leads, via a dynamic resolution process, to single atropisomers of tertiary amides bearing chiral imidazolidines or oxazolidines. Hydrolysis of the new heterocycle competes a dynamic thermodynamic resolution of the starting aldehyde, and rapid reduction allows the isolation of atropisomeric amides bearing 2-hydroxymethyl substituents in enantiomerically enriched form. Evidence that the reactions are under thermodynamic control is presented. (C) 2004 Elsevier Ltd. All rights reserved.
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