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Enantioselective ketone reductions convert prochiral ketones into chiral, non-racemic alcohols and are used heavily for the synthesis of stereodefined alcohols. [ 1 ] Carbonyl reduction, the net addition of H 2 across a carbon-oxygen double bond, is an important way to prepare alcohols.
For the α,β unsaturated systems 10-12, efficient reduction of the ketone occurs despite the possible side reaction of hydroboration of the C-C unsaturated bond. The CBS reduction has also been shown to tolerate the presence of heteroatoms as in ketone 13 , which is capable of coordinating to the borane.
The aluminium based Meerwein–Ponndorf–Verley reduction can be performed on prochiral ketones leading to chiral alcohols. The three main ways to achieve the asymmetric reduction is by use of a chiral alcohol hydride source, use of an intramolecular MPV reduction, or use of a chiral ligand on the aluminium alkoxide.
Barbas' collaborator List also extended the reaction to asymmetric prochiral ketones: List and Notz also revealed that proline and 5,5-dimethyl thiazolidinium-4-carboxylate appeared to be optimal catalysts within a large group of screened amines. [14] In 2002 the Macmillan group demonstrated a proline-catalyzed aldol reaction between aldehydes ...
In cases where the Grignard reagent is adding to an aldehyde or a prochiral ketone, the Felkin-Anh model or Cram's Rule can usually predict which stereoisomer will be formed. With easily deprotonated 1,3- diketones and related acidic substrates, the Grignard reagent RMgX functions merely as a base, giving the enolate anion and liberating the ...
Hydride addition as in a reduction process from this side will form the (S)-enantiomer and attack from the opposite Si-face will give the (R)-enantiomer. However, one should note that adding a chemical group to the prochiral center from the Re -face will not always lead to an ( S )-stereocenter, as the priority of the chemical group has to be ...