Consequently, several contributions by Felkin,8
Anh, and Eisenstein9 evolved into a new model,
which became subsequently known by the names of
its main developers as the Felkin-Anh rule (Scheme
4). The key idea was that the substituent L is placed
orthogonal to the carbonyl group, allowing the nucleophile
to attack anti to L, thus most effectively
avoiding steric repulsion. Moreover, the definition of
L was broadened in that electronic factors were
recognized to play a pivotal role in stabilizing the
transition state with the incoming nucleophile. Substituents
exhibiting an electron-withdrawing effect
are regarded as L independent of their steric bulk.
In this way, the low-lying ó*C-L orbital is aligned
parallel with the ð- and ð*-orbital of the carbonyl
group, allowing delocalization of electron density by
hyperconjugation from the reaction center toward L
(Figure 2). Moreover, the reaction pathway is advantageous
compared to the one starting from the Cram
conformation since it leads directly to a staggered
conformation in the product