Stereochemical outcome of benzyllithiums synthesis from selenides

A. Krief; M. Hobe; W. Dumont; E. Badaoui; E. Guittet; G. Evrard

doi:10.1016/S0040-4039(00)92094-X

Stereochemical outcome of benzyllithiums synthesis from selenides

A. Krief, M. Hobe, W. Dumont, E. Badaoui, E. Guittet, G. Evrard

Unit of organic chemistry

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

Abstract

Epimerisation usually occurs during the synthesis of arylalcanes from the corresponding benzylselenides which involves benzyllithiums as intermediates. This has been used to produce stereoselectively arylcyclopentanes and arylcyclopropanes. β-Benzenesulfonyloxyalkyl selenides substituted on the carbon bearing the benzenesulfonyl group behave differently and lead stereospecifically to arylcyclopropane derivatives.

Original language	English
Pages (from-to)	3381-3384
Number of pages	4
Journal	Tetrahedron Letters
Volume	33
Issue number	23
DOIs	https://doi.org/10.1016/S0040-4039(00)92094-X
Publication status	Published - 1 Jan 1992

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abstract = "Epimerisation usually occurs during the synthesis of arylalcanes from the corresponding benzylselenides which involves benzyllithiums as intermediates. This has been used to produce stereoselectively arylcyclopentanes and arylcyclopropanes. β-Benzenesulfonyloxyalkyl selenides substituted on the carbon bearing the benzenesulfonyl group behave differently and lead stereospecifically to arylcyclopropane derivatives.",

author = "A. Krief and M. Hobe and W. Dumont and E. Badaoui and E. Guittet and G. Evrard",

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AU - Krief, A.

AU - Hobe, M.

AU - Dumont, W.

AU - Badaoui, E.

AU - Guittet, E.

AU - Evrard, G.

PY - 1992/1/1

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N2 - Epimerisation usually occurs during the synthesis of arylalcanes from the corresponding benzylselenides which involves benzyllithiums as intermediates. This has been used to produce stereoselectively arylcyclopentanes and arylcyclopropanes. β-Benzenesulfonyloxyalkyl selenides substituted on the carbon bearing the benzenesulfonyl group behave differently and lead stereospecifically to arylcyclopropane derivatives.

AB - Epimerisation usually occurs during the synthesis of arylalcanes from the corresponding benzylselenides which involves benzyllithiums as intermediates. This has been used to produce stereoselectively arylcyclopentanes and arylcyclopropanes. β-Benzenesulfonyloxyalkyl selenides substituted on the carbon bearing the benzenesulfonyl group behave differently and lead stereospecifically to arylcyclopropane derivatives.

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DO - 10.1016/S0040-4039(00)92094-X

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ER -

Stereochemical outcome of benzyllithiums synthesis from selenides

Abstract

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