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

A. Krief; B. Kenda; B. Remacle

doi:10.1016/0040-4039(95)01641-T

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

A. Krief, B. Kenda, B. Remacle

Unite de recherche en chimie organique

Résultats de recherche: Contribution à un journal/une revue › Article › Revue par des pairs

Résumé

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.

langue originale	Anglais
Pages (de - à)	7917-7920
Nombre de pages	4
journal	Tetrahedron Letters
Volume	36
Numéro de publication	43
Les DOIs	https://doi.org/10.1016/0040-4039(95)01641-T
Etat de la publication	Publié - 1 janv. 1995

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10.1016/0040-4039(95)01641-T

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

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.",

author = "A. Krief and B. Kenda and B. Remacle",

year = "1995",

month = jan,

day = "1",

doi = "10.1016/0040-4039(95)01641-T",

language = "English",

volume = "36",

pages = "7917--7920",

journal = "Tetrahedron Letters",

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T1 - Stereoselective syntheses of 1,2-dialkyl-1-phenyl-cyclopentanes by intramolecular carbolithiation of vinyl sulfides

AU - Krief, A.

AU - Kenda, B.

AU - Remacle, B.

PY - 1995/1/1

Y1 - 1995/1/1

N2 - 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.

AB - 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.

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U2 - 10.1016/0040-4039(95)01641-T

DO - 10.1016/0040-4039(95)01641-T

M3 - Article

AN - SCOPUS:0028884510

SN - 0040-4039

VL - 36

SP - 7917

EP - 7920

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 43

ER -

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

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