Diastereo- and Enantioselective Synthesis of Hexa-1,5-diene-3,4-diamines by Cobalt-Catalyzed Asymmetric Double Allylic Amination
Abstract
A highly diastereo- and enantioselective synthesis of hexa-1,5-diene-3,4-diamines has been developed based on cobalt-catalyzed double allylic amination of hexa-1,5-diene-3,4-diyl dimethyl dicarbonate. Consecutive stereocenters can be built under an asymmetric double allylic substitution strategy. Acyclic hexa-1,5-diene-3,4-diamines and cyclic tetrahydroquinoxalines were synthesized in up to 96% yield, >20:1 dr, and normally 99% ee. Cobalt catalysts exhibit a uniquely high reactivity over rhodium and iridium by overcoming the coordinating inhibition of the diene structure of both substrates and products. The chiral hexa-1,5-diene-3,4-diamines were not only used as chiral ligands for Rh-catalyzed conjugated 1,4-addition but also transformed into chiral N-heterocyclic carbene precursors and other chiral products.
Fields of Study & Subjects
Asymmetric Hydrogenation and Catalysis
Asymmetric Synthesis and Catalysis
Cyclopropane Reaction Mechanisms
Publication details
- Journal / source
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Volume
- 28
- Issue
- 20
- Pages
- 6256–6262
- Publication date
- 12 May 2026
- Language
- EN