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

J. Bousbaa, F. Ooms, A. Krief

Research output: Contribution to journalArticle

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.
Original languageEnglish
Pages (from-to)7625-7628
Number of pages4
JournalTetrahedron Letters
Volume38
Issue number43
DOIs
Publication statusPublished - 27 Oct 1997

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