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

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Keywords

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

Cite this

Konstantinova, O., Sarabèr, F. C. E., Melguizo, E., Jansen, B. J. M., & de Groot, Æ. (2006). 1-phenylthio-3-vinyl-3-cyclohexenol, a new reagent for bis-annelation of silyl enol ethers. Tetrahedron, 62(8), 1749-1755. https://doi.org/10.1016/j.tet.2005.11.060

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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.",

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

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AU - Konstantinova, O.

AU - Sarabèr, F.C.E.

AU - Melguizo, E.

AU - Jansen, B.J.M.

AU - de Groot, Æ.

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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

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KW - vinylsilanes

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KW - cetones

U2 - 10.1016/j.tet.2005.11.060

DO - 10.1016/j.tet.2005.11.060

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Access to Document

10.1016/j.tet.2005.11.060