Diastereoselective Addition of Organometallic Reagents to Chiral Carbonyl Compounds

A diastereoselective addition of organometallic reagents to simple chiral ketones is generally more challenging than addition to aldehydes. Nucleophilic addition of organometallic reagents to carbonyl-containing substrates represents one of the crucial approaches. Additions of organometallic reagents to a cyclic carbonyl moiety are more complicated than in the case of acyclic ketones, where diastereoselectivity is predominantly affected by the configuration of the adjacent chiral center(s). Diastereoselective additions of organometallic reagents to chiral carbonyl compounds have been used for the synthesis of a variety of natural, biologically active, and structurally interesting compounds. Diastereoselectivity of 1,2-addition is affected not only by the stereochemistry of the carbonyl substrate and the characteristics of the organometallic reagent but also by many other factors including R solvent, temperature, additive, and specific features of the substrate or organometallic reagent. The presence of stereogenic center in organometallic reagents or carbonyl compounds leads to diastereoisomers.