Continuum of Mechanisms for Nucleophilic Substitutions of Cyclic Acetals
Organic Letters2008Vol. 10(21), pp. 4907–4910
Citations Over TimeTop 10% of 2008 papers
Abstract
The effect of nucleophile strength on diastereoselectivity in the nucleophilic substitution of cyclic acetals was explored. Stereoselectivity remained constant and high as nucleophilicity increased until a threshold value was reached. Beyond this point, however, selection of Lewis acid determined whether stereochemical inversion or erosion was observed.
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