Theoretical studies of the role of complexation in the conjugate addition of dialkylcuprates to electron-deficient CC bonds. Influence on the stereochemistry of the reaction
- 1 January 1989
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 24,p. 1884-1886
- https://doi.org/10.1039/c39890001884
Abstract
Ab initio molecular orbital calculations suggest that dialkylcuprates add to conjugated CC bonds via a mechanism which involves pre-complexation of the copper centre with the double bond, implying an acute angle of attack onto the CC bond; this may explain the opposite stereoselectivities observed in the reactions of dialkylcuprates on the one hand and of alkylcopper reagents (and other conventional nucleophiles) on the other.Keywords
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