Use of chiral B(III) complexes in the cycloaddition of C,N-diphenylnitroneto tert-butyl vinyl ether

Authors
Bayon, P de March, P Figueredo, M Font, J Medrano, J
Citation
P. Bayon et al., Use of chiral B(III) complexes in the cycloaddition of C,N-diphenylnitroneto tert-butyl vinyl ether, TETRAHEDR-A, 11(21), 2000, pp. 4269-4278
Citations number
48
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
11
Issue
21
Year of publication
2000
Pages
4269 - 4278
Database
ISI
SICI code
0957-4166(20001103)11:21<4269:UOCBCI>2.0.ZU;2-S
Abstract
The 1,3-dipolar cycloaddition of C,N-diphenylnitrone to tert-butyl vinyl et her in the presence of several chiral B(III) complexes which incorporate di fferent bidentate ligands has been investigated. The use of these B(III) sp ecies reverses the endo/exo diastereoselectivity in relation to the uncatal ysed reaction, giving trans cycloadducts as major products. Some of the cat alysts gave very fast and high yielding reactions, but the enantioselectivi ties were only low to moderate. (C) 2000 Elsevier Science Ltd. All rights r eserved.