Intramolecular Reactions of Temporarily Silicon-Tethered Molecules

Louis Fensterbank; Max Malacria; Scott Mc N. Sieburth

doi:10.1055/s-1997-1295

Synthesis 1997; 1997(8): 813-854
DOI: 10.1055/s-1997-1295

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Intramolecular Reactions of Temporarily Silicon-Tethered Molecules

Louis Fensterbank¹ , Max Malacria² , Scott McN. Sieburth³

¹Université Pierre et Marie Curie, Laboratoire de Chimie Organique de Synthèse, associé au CNRS, Tour 44-54, 3229, 4 Place Jussieu, 75252 Paris Cedex, France, E-mail: fensterb@ccr.jussieu.fr
²Université Pierre et Marie Curie, Laboratoire de Chimie Organique de Synthèse, associé au CNRS, Tour 44-54, 3229, 4 Place Jussieu, 75252 Paris Cedex, France, E-mail: malacria@ccr.jussieu.fr
³Department of Chemistry, State University of New York at Stony Brook, Stony Brook, New York 11794-3400, USA, E-mail: SSIEBURTH@notes.cc.sunysb.edu

Abstract

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The Temporary Silicon Connection transforms a potential intermolecular reaction into an intramolecular one, by transiently connecting both partners through a silicon linkage. In addition to entropic advantages, temporary connectivity forces regioselectivity and high stereoselectivity often results. Applications in radical cyclizations, cycloadditions, nucleophilic delivery, and hydrosilylation are discussed. Connection is also ensured by the coordination of an aldehyde to a Lewis acidic silicon and has served in aldol and allylation reactions.

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