SYNTHESIS OF 1,3-DIENES OF (E,Z) CONFIGURATION BY A 3-COMPONENT COUPLING STRATEGY

Authors
WHITE JD JENSEN MS
Citation
Jd. White et Ms. Jensen, SYNTHESIS OF 1,3-DIENES OF (E,Z) CONFIGURATION BY A 3-COMPONENT COUPLING STRATEGY, Tetrahedron, 51(20), 1995, pp. 5743-5756
Citations number
24
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
51
Issue
20
Year of publication
1995
Pages
5743 - 5756
Database
ISI
SICI code
0040-4020(1995)51:20<5743:SO1O(C>2.0.ZU;2-M
Abstract
Three-component coupling of an anionic nucleophile, butadienyltripheny lphosphonium bromide, and an aldehyde gave conjugated dienes of predom inantly (E,Z) configuration. Dianions of beta-dicarbonyl systems and d icarboxylic acids, and monoanions of sulfones were employed as nucleop hiles. Stereoselectivity in favor of an(E,Z)-1,3-diene was highest whe n a beta-dicarbonyl dianion was used in conjunction with an alpha-bran ched aldehyde.