Boranes reaction with halo carbonyl compounds

Carbon-carbon bonds can also be made with alkyl boranes. The requirement for a carbon nucleophile that bears a suitable leaving group is met by a-halo carbonyl compounds. The halogen makes enolization of the carbonyl compound easier and then departs in the rearrangement step. The product is a boron enolate with the boron bound to carbon. Under the basic conditions of the reaction, hydrolysis to the corresponding carbonyl compound is rapid. 

Reaction of halo ketones or diazo ketones with boranes 0-102 Carbonylation of alkyl halides 0-104 Reaction between acyl halides and organometallic compounds 0-105 Reaction between other acid derivatives and organometallic compounds... 

Reactions of chiral allylic boranes with carbonyl compounds Reactions of chiral allyl boranes with imines Asymmetric Addition of Carbon Nucleophiles to Ketones Addition of alkyl lithiums to ketones Asymmetric epoxidation with chiral sulfur ylids Asymmetric Nucleophilic Attack by Chiral Alcohols Deracemisation of arylpropionic acids Deracemisation of a-halo acids Asymmetric Conjugate Addition of Nitrogen Nucleophiles An asymmetric synthesis of thienamycin Asymmetric Protonation... 

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