CATALYSIS BY TEMPORARY COVALENT ACTIVATION - A NOVEL CATALYSIS OF UNACTIVATED DIELS-ALDER REACTIONS

Authors
SINGLETON DA LEUNG SW MARTINEZ JP LEE YK
Citation
Da. Singleton et al., CATALYSIS BY TEMPORARY COVALENT ACTIVATION - A NOVEL CATALYSIS OF UNACTIVATED DIELS-ALDER REACTIONS, Tetrahedron letters, 38(18), 1997, pp. 3163-3166
Citations number
20
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
18
Year of publication
1997
Pages
3163 - 3166
Database
ISI
SICI code
0040-4039(1997)38:18<3163:CBTCA->2.0.ZU;2-3
Abstract
Diels-Alder reactions of cis-2-chlorovinyltributylstannane are greatly accelerated by tbe presence of catalytic amounts of haloboranes. Mech anistic studies support a mechanism for the catalysis involving an int ermediate boron-activated dienophile. A similar but simpler catalysis of Diels-Alder reactions of unactivated alkynes, via a hydroboration - Diels-Alder - dehydroboration mechanism, is also described. (C) 1997 Elsevier Science Ltd.