Theoretical evidence in support of the Anh–Eisenstein electronic model in controlling π-facial stereoselectivity in nucleophilic additions to carbonyl compounds
- 1 January 1990
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 6,p. 456-458
- https://doi.org/10.1039/c39900000456
Abstract
Ab initio MO calculations on the complete set of diastereoisomeric transition structures for the addition of cyanide anion to propanal, fluoroethanal, and 2-fluoropropanal, revealed that the most stable transition structure has the C–F bond in the antiperiplanar position with respect to the forming carbon-nucleophile bond; this finding is consistent with the Anh–Eisenstein model for nucleophilic attack on chiral acyclic carbonyl compounds but not with the Cieplak model.Keywords
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