SITE AND STEREOSELECTIVITY OF THE CYCLOPROPANATION OF UNSYMMETRICALLYSUBSTITUTED 1,3-DIENES BY THE SIMMONS-SMITH REACTION

Authors
GUERREIRO MC SCHUCHARDT U
Citation
Mc. Guerreiro et U. Schuchardt, SITE AND STEREOSELECTIVITY OF THE CYCLOPROPANATION OF UNSYMMETRICALLYSUBSTITUTED 1,3-DIENES BY THE SIMMONS-SMITH REACTION, Synthetic communications, 26(9), 1996, pp. 1793-1800
Citations number
13
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synthetic communications → ACNP
ISSN journal
00397911
Volume
26
Issue
9
Year of publication
1996
Pages
1793 - 1800
Database
ISI
SICI code
0039-7911(1996)26:9<1793:SASOTC>2.0.ZU;2-M
Abstract
In the Simmons-Smith reaction, 1,3-dienes are preferentially cycloprop anated at the more electron-rich double bond to afford the trans-vinyl cyclopropane; an allylic hydroxyl group increases the reactivity and d irects the cyclopropanation to the adjacent double bond.