Stereoselectivity control in reactions of tertiary 2-oxacycloalkyl radicals

DOI: 10.1055/s-1997-1346

Source and publish data:

Synthesis p. 1261 - 1267 (1997)

Update date:2022-08-04

Topics:

Authors:

Gerster Gerster

Renaud Renaud

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Article abstract of DOI:10.1055/s-1997-1346

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.

Full text of DOI:10.1055/s-1997-1346

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