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

Olga Konstantinova; Florence C.E. Sarabèr; Enrique Melguizo; Ben J.M. Jansen; Aede 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

Olga Konstantinova, Florence C.E. Sarabèr, Enrique Melguizo, Ben J.M. Jansen, Aede De Groot^*

^*Corresponding author for this work

Not published at Aalto University

Research output: Contribution to journal › Article › Scientific › 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 enol 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
Number of pages	7
Journal	Tetrahedron
Volume	62
Issue number	8
DOIs	https://doi.org/10.1016/j.tet.2005.11.060
Publication status	Published - 20 Feb 2006
MoE publication type	A1 Journal article-refereed

Keywords

1-Phenylthio-3-vinyl-cyclohex-1-en-3-ol
Addition
Bis-annelation
Silyl enol ethers

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10.1016/j.tet.2005.11.060

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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 enol 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.",

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

AU - Konstantinova, Olga

AU - Sarabèr, Florence C.E.

AU - Melguizo, Enrique

AU - Jansen, Ben J.M.

AU - De Groot, Aede

PY - 2006/2/20

Y1 - 2006/2/20

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 enol 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 enol 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 - 1-Phenylthio-3-vinyl-cyclohex-1-en-3-ol

KW - Addition

KW - Bis-annelation

KW - Silyl enol ethers

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U2 - 10.1016/j.tet.2005.11.060

DO - 10.1016/j.tet.2005.11.060

M3 - Article

AN - SCOPUS:31444447437

SN - 0040-4020

VL - 62

SP - 1749

EP - 1755

JO - Tetrahedron

JF - Tetrahedron

IS - 8

ER -

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

Abstract

Keywords

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