Stereochemical outcome of reactions involving 1,1-bis(seleno) 4-tert-butyl cyclohexanes

A. Krief, E. Badaoui, W. Dumont, L. Hevesi, B. Hermans, R. Dieden

Research output: Contribution to journalArticle

Abstract

Stereoselective allylation of conformationally rigid 4-tert-butyl-1,1-bis(methylseleno) cyclohexanes has been achieved (i) from the axial face on sequential reaction with alkyllithiums, copper iodide-dimethyl sulfide and allyl bromides and (ii) from the equatorial face of reaction with allyl stannanes or -silanes in the presence of a Lewis acid. The synthesis of 1-selenocyclohexane has been achieved via the 'carbanionic route' or with tin hydride through a 'radical route'. The former reaction leads selectively to the trans selenides whereas both stereoisomers are produced in the latter process.
Original languageEnglish
Pages (from-to)3231-3234
Number of pages4
JournalTetrahedron Letters
Volume32
Issue number27
DOIs
Publication statusPublished - 1 Jan 1991

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Cyclohexanes
Allylation
Silanes
Lewis Acids
Stereoisomerism
Tin
Iodides
Hydrides
Copper
dimethyl sulfide
stannane
allyl bromide

Cite this

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abstract = "Stereoselective allylation of conformationally rigid 4-tert-butyl-1,1-bis(methylseleno) cyclohexanes has been achieved (i) from the axial face on sequential reaction with alkyllithiums, copper iodide-dimethyl sulfide and allyl bromides and (ii) from the equatorial face of reaction with allyl stannanes or -silanes in the presence of a Lewis acid. The synthesis of 1-selenocyclohexane has been achieved via the 'carbanionic route' or with tin hydride through a 'radical route'. The former reaction leads selectively to the trans selenides whereas both stereoisomers are produced in the latter process.",
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Stereochemical outcome of reactions involving 1,1-bis(seleno) 4-tert-butyl cyclohexanes. / Krief, A.; Badaoui, E.; Dumont, W.; Hevesi, L.; Hermans, B.; Dieden, R.

In: Tetrahedron Letters, Vol. 32, No. 27, 01.01.1991, p. 3231-3234.

Research output: Contribution to journalArticle

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T1 - Stereochemical outcome of reactions involving 1,1-bis(seleno) 4-tert-butyl cyclohexanes

AU - Krief, A.

AU - Badaoui, E.

AU - Dumont, W.

AU - Hevesi, L.

AU - Hermans, B.

AU - Dieden, R.

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Y1 - 1991/1/1

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