INTERMOLECULAR ALDOL REACTIONS VIA ALLYLIC O-STANNYL KETYLS

Authors
ENHOLM EJ WHITLEY PE
Citation
Ej. Enholm et Pe. Whitley, INTERMOLECULAR ALDOL REACTIONS VIA ALLYLIC O-STANNYL KETYLS, Tetrahedron letters, 36(50), 1995, pp. 9157-9160
Citations number
18
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
36
Issue
50
Year of publication
1995
Pages
9157 - 9160
Database
ISI
SICI code
0040-4039(1995)36:50<9157:IARVAO>2.0.ZU;2-R
Abstract
A mild and neutral free radical reaction of an alpha,beta-unsaturated ketone and tributyltin radical produced a resonance-stabilized allylic O-stannyl ketyl intermediate. A tin(IV) enolate, produced by subseque nt hydrogen atom transfer, was next quenched with various aldehydes to yield an aldol product which was readily eliminated with p-toluenesul fonic acid to afford new alpha,beta-unsaturated ketones with E/Z ratio s up to >100:1.