Metal, ligand and protective group tuning as a means to control selectivity

Abstract

Chemo- and stereoselective Grignard addition reactions are possible if ligand tuning is applied, as in the magnesiation of alkyllithium reagents with magnesium tosylates or carboxylates. Protective groups tuning is another important instrument. Thus, N,N-dibenzyl-amino aldehydes react with a variety of organometallics under non-chelation control. The nature of the protective group is also important in reactions of a-amino aldimines and electron-poor y-aminoolefins (including peptide derivatives). © 1992 IUPAC