1-phenylthio-3-vinyl-3-cyclohexenol, a new reagent for bis-annelation of silyl enol ethers

O. Konstantinova; F.C.E. Sarabèr; E. Melguizo; B.J.M. Jansen; Æ. de Groot

doi:10.1016/j.tet.2005.11.060

1-phenylthio-3-vinyl-3-cyclohexenol, a new reagent for bis-annelation of silyl enol ethers

O. Konstantinova, F.C.E. Sarabèr, E. Melguizo, B.J.M. Jansen, Æ. de Groot

Research output: Contribution to journal › Article › Academic › peer-review

Abstract

1-Phenylthio-3-vinyl-cyclohex-1-en-3-ol (2) has been synthesized and investigated as a new bis-annelation reagent for silyl enol ethers. Reagent 2 can be synthesized by a Grignard reaction of vinyl magnesium bromide with 3-phenylthiocyclohexenone. The reaction with silyl cool ethers takes place Under Lewis acid catalysis and generally proceeds in good yields. The resulting phenylthiodienes can be hydrolyzed to enones, which have been cyclized in a homologous aldol reaction to polycyclic compounds.

Original language	English
Pages (from-to)	1749-1755
Journal	Tetrahedron
Volume	62
Issue number	8
DOIs	https://doi.org/10.1016/j.tet.2005.11.060
Publication status	Published - 2006

Keywords

noyau cyclopentanonaphtalenique hydrogene
la synthese totale
d-homo-steroids
isoxazole annelation
vinyl ketones
efficient
vinylsilanes
sterolique
cetones

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@article{38179a620eec4f6fa5f91d0ce965d023,

title = "1-phenylthio-3-vinyl-3-cyclohexenol, a new reagent for bis-annelation of silyl enol ethers",

abstract = "1-Phenylthio-3-vinyl-cyclohex-1-en-3-ol (2) has been synthesized and investigated as a new bis-annelation reagent for silyl enol ethers. Reagent 2 can be synthesized by a Grignard reaction of vinyl magnesium bromide with 3-phenylthiocyclohexenone. The reaction with silyl cool ethers takes place Under Lewis acid catalysis and generally proceeds in good yields. The resulting phenylthiodienes can be hydrolyzed to enones, which have been cyclized in a homologous aldol reaction to polycyclic compounds.",

keywords = "noyau cyclopentanonaphtalenique hydrogene, la synthese totale, d-homo-steroids, isoxazole annelation, vinyl ketones, efficient, vinylsilanes, sterolique, cetones",

author = "O. Konstantinova and F.C.E. Sarab{\`e}r and E. Melguizo and B.J.M. Jansen and {de Groot}, {\AE}.",

note = "ISI Document Delivery No.: 013MT Times Cited: 0 Cited Reference Count: 38",

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doi = "10.1016/j.tet.2005.11.060",

language = "English",

volume = "62",

pages = "1749--1755",

journal = "Tetrahedron",

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publisher = "Elsevier",

number = "8",

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TY - JOUR

T1 - 1-phenylthio-3-vinyl-3-cyclohexenol, a new reagent for bis-annelation of silyl enol ethers

AU - Konstantinova, O.

AU - Sarabèr, F.C.E.

AU - Melguizo, E.

AU - Jansen, B.J.M.

AU - de Groot, Æ.

N1 - ISI Document Delivery No.: 013MT Times Cited: 0 Cited Reference Count: 38

PY - 2006

Y1 - 2006

N2 - 1-Phenylthio-3-vinyl-cyclohex-1-en-3-ol (2) has been synthesized and investigated as a new bis-annelation reagent for silyl enol ethers. Reagent 2 can be synthesized by a Grignard reaction of vinyl magnesium bromide with 3-phenylthiocyclohexenone. The reaction with silyl cool ethers takes place Under Lewis acid catalysis and generally proceeds in good yields. The resulting phenylthiodienes can be hydrolyzed to enones, which have been cyclized in a homologous aldol reaction to polycyclic compounds.

AB - 1-Phenylthio-3-vinyl-cyclohex-1-en-3-ol (2) has been synthesized and investigated as a new bis-annelation reagent for silyl enol ethers. Reagent 2 can be synthesized by a Grignard reaction of vinyl magnesium bromide with 3-phenylthiocyclohexenone. The reaction with silyl cool ethers takes place Under Lewis acid catalysis and generally proceeds in good yields. The resulting phenylthiodienes can be hydrolyzed to enones, which have been cyclized in a homologous aldol reaction to polycyclic compounds.

KW - noyau cyclopentanonaphtalenique hydrogene

KW - la synthese totale

KW - d-homo-steroids

KW - isoxazole annelation

KW - vinyl ketones

KW - efficient

KW - vinylsilanes

KW - sterolique

KW - cetones

U2 - 10.1016/j.tet.2005.11.060

DO - 10.1016/j.tet.2005.11.060

M3 - Article

VL - 62

SP - 1749

EP - 1755

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 8

ER -