Highly diastereoselective synthesis of vinylcyclopropane derivatives with (-)-8-phenylmenthol as chiral auxiliary

Authors
Ye, S Tang, Y Dai, LX
Citation
S. Ye et al., Highly diastereoselective synthesis of vinylcyclopropane derivatives with (-)-8-phenylmenthol as chiral auxiliary, J ORG CHEM, 66(17), 2001, pp. 5717-5722
Citations number
36
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
66
Issue
17
Year of publication
2001
Pages
5717 - 5722
Database
ISI
SICI code
0022-3263(20010824)66:17<5717:HDSOVD>2.0.ZU;2-9
Abstract
The silylated telluronium. allylide 4, generated in situ from the correspon ding telluronium salt in the presence of LiTMP, reacted with (-)-8-phenylme nthyl alpha,beta -unsaturated esters to afford trans-2-silylvinyl-trans-3-s ubstituted cyclopropyl esters with high diastereoselectivity in high yields . The absolute configuration was determined by chemical transformation. A m echanistic rationale is proposed.