sigma-pi chelation-controlled chemoselective ring openings of epoxides

Authors
Asao, N Kasahara, T Yamamoto, Y
Citation
N. Asao et al., sigma-pi chelation-controlled chemoselective ring openings of epoxides, TETRAHEDR L, 42(44), 2001, pp. 7903-7905
Citations number
23
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
44
Year of publication
2001
Pages
7903 - 7905
Database
ISI
SICI code
0040-4039(20011029)42:44<7903:SCCROO>2.0.ZU;2-B
Abstract
The chemoselective ring opening of alkynyl epoxides in the co-existence of the corresponding alkyl epoxides is achieved in the Me3Al mediated reaction with alkynyllithium reagents. The observed interesting chemoselectivity is most probably a reflection of bidentate complexation of the Lewis acid to an n-electron of an oxygen atom of the epoxide and pi -electrons of the C C triple bond. (C) 2001 Elsevier Science Ltd. All rights reserved.