1,2-Additions on Chiral N-Sulfinylketimines: An Easy Access to Chiral α-Tertiary Amines

Chiral alpha-tertiary amines, a motif present in alpha,alpha-disubstituted alpha-amino acids, in a wide range of natural products, and many drugs and drug candidates, are important targets in organic chemistry. Among the possible strategies, 1,2-addition to chiral N-sulfinyl-ketimines is one of the best routes to form chiral alpha-tertiary amines with a high level of stereoselectivity. In this review, we focus first on the addition of organometallic reagents or other nucleophiles as enols or ylides to chiral N-sulfinylketimines. Then secondly we cover a selection of applications of these additions in the synthesis of valuable biologically active compounds.

Automated summary

Chiral alpha-tertiary amines, a motif found in various natural products, drugs, and drug candidates, can be synthesized by adding organometallic reagents or other nucleophiles to chiral N-sulfinylketimines. This synthetic strategy has wide applications in the synthesis of biologically active compounds.