Preparation of 1-Hydroxycyclopentanecarboxylic Acid Derivatives from a Chiral Equivalent of Glycolic Acid

Abazi, Sokol; Rapado, Liliana Parra; Schenk, Kurt; Renaud, Philippe

doi:10.1002/(sici)1099-0690(199902)1999:2<477::aid-ejoc477>3.3.co;2-6

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“…Interestingly, the reactions became more selective when the reactivity of the radical trap was enhanced (Scheme 18) [40]. This is clearly contrary to the reactivityselectivity principle and is best explained by the position of the transition state.…”

Section: Position Of the Transition Statementioning

confidence: 99%

Stereoselectivity of Radical Reactions: Cyclic Systems

Renaud¹

2001

Radicals in Organic Synthesis

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Cyclic radicals are very often involved in the key step of a reaction sequence. They are particularly useful since the stereochemical outcome of their reactions can be easily predicted and in some cases directed. Selected examples from the recent literature have been chosen in order to illustrate the different factors governing the stereochemical outcome. The importance of steric effects, conformational effects, neighboring prochiral centers, pyramidalization, stereoelectronic effects and position of the transition states will be discussed based on examples of synthetic importance. The anti RuleCyclic radicals can only exist in a reduced number of conformations relative to acyclic ones. Therefore, prediction of the stereochemistry is simplified. As nicely documented in two excellent review articles [ l , 21, the anti rule could be applied with great success to many cases of cyclic radicals: reactions occur preferentially in unti fashion to the substituents present in the cyclic moiety. This simple model is based on minimization of steric interactions in the transition state and is particularly efficient when the conformation of the radical intermediate is known.

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Section: Position Of the Transition Statementioning

confidence: 99%