The importance of electrostatic effects in controlling π-facial stereoselectivity in nucleophilic additions to carbonyl compounds: an ab initio MO study of a prototype chelation model
- 1 January 1991
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 5,p. 327-330
- https://doi.org/10.1039/c39910000327
Abstract
Ab initio MO calculations on the complete set of diastereoisomeric transition structures for the addition of lithium hydride to fluoroethanal and 2-fluoropropanal revealed that the most stable transition structure for each system is dominated by electrostatic attraction between Li and F and this results in the formation of the Cram chelation control product for the latter aldehyde.Keywords
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