Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 41, Pages 12087-12090Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201503525
Keywords
allylic compounds; carbocations; nucleophilic substitution; synthetic methods; through-space interactions
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Funding
- National Institutes of Health, National Institute of General Medical Sciences [GM-61066]
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Nucleophilic substitution reactions of acetals having benzyloxy groups four carbon atoms away can be highly diastereoselective. The selectivity in several cases increased as the reactivity of the nucleophile increased, in violation of the reactivity/selectivity principle. The increase in selectivity with reactivity suggests that multiple conformational isomers of reactive intermediates can give rise to the products.
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