γ-Siloxy-benzyllithiums: Stereochemistry of the retro-[1,4]-Brook rearrangement

J. Bousbaa; F. Ooms; A. Krief

doi:10.1016/S0040-4039(97)01810-8

γ-Siloxy-benzyllithiums: Stereochemistry of the retro-[1,4]-Brook rearrangement

J. Bousbaa, F. Ooms, A. Krief

Unite de recherche en chimie organique

Résultats de recherche: Contribution à un journal/une revue › Article › Revue par des pairs

Résumé

Although γ-sulfonyloxy-benzylselenides react with butyllithium to produce stereospecifically aryl cyclopropanes, the corresponding γ-silyloxy-benzylselenides lead to a stereoisomeric mixture of γ-hydroxy-α-silyl-benzylselenides via the retro-[1,4]-Brook rearrangement. Apparently the intermediate benzyllithiums are alkylated before epimerisation takes place in the first case, whereas in the second one epimerisation occurs prior to the silyl group migration.

langue originale	Anglais
Pages (de - à)	7625-7628
Nombre de pages	4
journal	Tetrahedron Letters
Volume	38
Numéro de publication	43
Les DOIs	https://doi.org/10.1016/S0040-4039(97)01810-8
Etat de la publication	Publié - 27 oct. 1997

Accès au document

10.1016/S0040-4039(97)01810-8

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Contient cette citation

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abstract = "Although γ-sulfonyloxy-benzylselenides react with butyllithium to produce stereospecifically aryl cyclopropanes, the corresponding γ-silyloxy-benzylselenides lead to a stereoisomeric mixture of γ-hydroxy-α-silyl-benzylselenides via the retro-[1,4]-Brook rearrangement. Apparently the intermediate benzyllithiums are alkylated before epimerisation takes place in the first case, whereas in the second one epimerisation occurs prior to the silyl group migration.",

author = "J. Bousbaa and F. Ooms and A. Krief",

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T1 - γ-Siloxy-benzyllithiums

T2 - Stereochemistry of the retro-[1,4]-Brook rearrangement

AU - Bousbaa, J.

AU - Ooms, F.

AU - Krief, A.

PY - 1997/10/27

Y1 - 1997/10/27

N2 - Although γ-sulfonyloxy-benzylselenides react with butyllithium to produce stereospecifically aryl cyclopropanes, the corresponding γ-silyloxy-benzylselenides lead to a stereoisomeric mixture of γ-hydroxy-α-silyl-benzylselenides via the retro-[1,4]-Brook rearrangement. Apparently the intermediate benzyllithiums are alkylated before epimerisation takes place in the first case, whereas in the second one epimerisation occurs prior to the silyl group migration.

AB - Although γ-sulfonyloxy-benzylselenides react with butyllithium to produce stereospecifically aryl cyclopropanes, the corresponding γ-silyloxy-benzylselenides lead to a stereoisomeric mixture of γ-hydroxy-α-silyl-benzylselenides via the retro-[1,4]-Brook rearrangement. Apparently the intermediate benzyllithiums are alkylated before epimerisation takes place in the first case, whereas in the second one epimerisation occurs prior to the silyl group migration.

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DO - 10.1016/S0040-4039(97)01810-8

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

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