Continuum of Mechanisms for Nucleophilic Substitutions of Cyclic Acetals
- 10 October 2008
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 10 (21) , 4907-4910
- https://doi.org/10.1021/ol8019956
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.Keywords
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