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Synthesis 1997; 1997(11): 1261-1267
DOI: 10.1055/s-1997-1346
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Stereoselectivity Control in Reactions of Tertiary 2-Oxacycloalkyl Radicals

Michèle Gerster, Philippe Renaud*
  • *Institut de Chimie Organique, Université de Fribourg, Pérolles, CH-1700 Fribourg, Switzerland, Fax 41(0)263009739; E-mail: philippe.renaud@unifr.ch
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Publication Date:
31 December 2000 (online)

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The stereochemical outcome of reactions mediated by tertiary 1,3-dioxolan-4-yl and oxiranyl cyclic radicals has been investigated. The presence of a very bulky substituent next to the radical center has a remarkable syn directing effect. These stereoselectivities are rationalized by a model which takes into account radical pyramidalization, steric interactions between the substituents attached to the cycle and steric interactions with the incoming radical trap.

cyclic radicals - stereochemistry - asymmetric synthesis - model - pyramidalization