Stereoselective syntheses of 1,2-dialkyl-1-phenyl-cyclopentanes by intramolecular carbolithiation of vinyl sulfides

A. Krief, B. Kenda, B. Remacle

Research output: Contribution to journalArticlepeer-review

Abstract

6-Methylseleno-6-phenyl-1-phenylthio-1-heptene and 7-methylseleno-7-phenyl-2-phenylthio-2-octene produce 1-phenyl-2-(1'-phenylthioethyl)-cyclopentanes with high stereocontrol at all the three stereogenic centers on sequential reaction with butyllithium and methyl iodide or methanol respectively. Depending upon the solvent used, the derivative in which the methyl- and the phenylthio group are cis (THF) or trans (pentane) one to the other are selectively formed.
Original languageEnglish
Pages (from-to)7917-7920
Number of pages4
JournalTetrahedron Letters
Volume36
Issue number43
DOIs
Publication statusPublished - 1 Jan 1995

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