Asymmetric Induction - Carbonyl 1,2 Asymmetric Induction - Felkin-Anh Model

The Felkin-Anh model is an extension of the Felkin model that incorporates improvements suggested by Nguyen T. Anh and O. Eisenstein to correct for two key weaknesses in Felkin's model. The first weakness addressed was the statement by Felkin of a strong polar effect in nucleophilic addition transition states, which leads to the complete inversion of stereochemistry by SN2 reactions, without offering justifications as to why this phenomenon was observed. Anh's solution was to offer the antiperiplanar effect as a consequence of asymmetric induction being controlled by both substituent and orbital effects. In this effect, the best nucleophile acceptor σ* orbital is aligned parallel to both the π and π* orbitals of the carbonyl, which provide stabilization of the incoming anion.

The second weakness in the Felkin Model was the assumption of substituent minimization around the carbonyl R, which cannot be applied to aldehydes.

Incorporation of Bürgi–Dunitz angle ideas allowed Anh to postulate a non-perpendicular attack by the nucleophile on the carbonyl center, anywhere from 95° to 105° relative to the oxygen-carbon double bond, favoring approach closer to the smaller substituent and thereby solve the problem of predictability for aldehydes.

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