TANDEM ASYMMETRIC CYCLOPROPANATION COPE REARRANGEMENT - A HIGHLY DIASTEREOSELECTIVE AND ENANTIOSELECTIVE METHOD FOR THE CONSTRUCTION OF 1,4-CYCLOHEPTADIENES/

Authors
DAVIES HML STAFFORD DG DOAN BD HOUSER JH
Citation
Hml. Davies et al., TANDEM ASYMMETRIC CYCLOPROPANATION COPE REARRANGEMENT - A HIGHLY DIASTEREOSELECTIVE AND ENANTIOSELECTIVE METHOD FOR THE CONSTRUCTION OF 1,4-CYCLOHEPTADIENES/, Journal of the American Chemical Society, 120(14), 1998, pp. 3326-3331
Citations number
58
Categorie Soggetti
Chemistry
Journal title
Journal of the American Chemical Society → ACNP
ISSN journal
00027863
Volume
120
Issue
14
Year of publication
1998
Pages
3326 - 3331
Database
ISI
SICI code
0002-7863(1998)120:14<3326:TACCR->2.0.ZU;2-H
Abstract
Decomposition of vinyldiazoacetates by rhodium(II) (N-dodecylbenzenesu lfonyl)prolinate (Rh-2(S-DOSP)(4), 1) in the presence of dienes result s in a direct and highly enantioselective method for the formation of cis-divinylcyclopropanes. Combination of this process with a subsequen t Cope rearrangement results in a highly enantioselective synthesis of a variety of cycloheptadienes containing multiple stereogenic centers .