Stereocontrol in reactions of cyclic and acyclic β-silyl radicals

Stereocontrol in reactions of cyclic and acyclic β-silyl radicals

1,2-Stereocontrol in reactions of chiral beta-silylcarboradicals is discussed, with examples of stereoinduction arising from bromination, selenenylation, azidation, and 5-exo-trig cyclizations. Transition state models, based on A1,3 interactions and torsional strain have been proposed which allow fo...

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Veröffentlicht in:Comptes rendus. Chimie 2005-05, Vol.8 (5), p.823-832
1. Verfasser: LANDAIS, Yannick
Format: Artikel
Sprache:eng
Schlagworte:
Chemistry
Exact sciences and technology
Free radicals chemistry
Organic chemistry
Reactivity and mechanisms
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Zusammenfassung:1,2-Stereocontrol in reactions of chiral beta-silylcarboradicals is discussed, with examples of stereoinduction arising from bromination, selenenylation, azidation, and 5-exo-trig cyclizations. Transition state models, based on A1,3 interactions and torsional strain have been proposed which allow for reliable predictions of the stereochemical course of these processes. These models parallel those developed earlier in ionic (electrophilic and nucleophilic) processes.
ISSN:1631-0748
1878-1543
1878-1543
DOI:10.1016/j.crci.2005.02.012