Enantioselective Allylboration ofN-Trimethylsilylketimines

Significance

The article reports a novel enantio­selective synthesis of substituted primary α-allylethylamines from nitriles via the asymmetric allylation of N-trimethylsilylketimines. The resulting products are useful synthetic intermediates, for instance, for the preparation of chiral β-amino acids. This is the first example of a successful asymmetric allylboration of achiral imines, which demonstrates the power of the allylboration methodology, developed by the group of Soderquist, in asymmetric synthesis. Further elaboration of products into amino acid derivatives is also described.