STEREOSELECTIVE SYNTHESES OF 1,2-DIALKYL-1-PHENYL-CYCLOPENTANES BY INTRAMOLECULAR CARBOLITHIATION OF VINYL SULFIDES

Authors
KRIEF A KENDA B REMACLE B
Citation
A. Krief et al., STEREOSELECTIVE SYNTHESES OF 1,2-DIALKYL-1-PHENYL-CYCLOPENTANES BY INTRAMOLECULAR CARBOLITHIATION OF VINYL SULFIDES, Tetrahedron letters, 36(43), 1995, pp. 7917-7920
Citations number
13
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
36
Issue
43
Year of publication
1995
Pages
7917 - 7920
Database
ISI
SICI code
0040-4039(1995)36:43<7917:SSO1BI>2.0.ZU;2-1
Abstract
6-Methylseleno-6-phenyl-1-phenyithio-1-heptene and 7-methylseleno-7-ph enyl-2-phenylthio-2-octene produce 1-phenyl-2-(1'-phenylthioethyl)-cyc lopentanes with high stereocontrol at all the three stereogenic center s on sequential reaction with butyllithium and methyl iodide or methan ol respectively. Depending upon the solvent used, the derivative in wh ich the methyl- and the phenylthio group are cis (THF) or trans (penta ne) one to the other are selectively formed.