Desymmetrizing Isomerization of Alkene via Thiazolinyl Iminoquinoline Cobalt Catalysis

We report a cobalt-catalyzed desymmetrizing isomerization of exocyclic alkenes to generate chiral 1-methylcyclohexene derivatives with good yields and enantioselectivities. A novel chiral thiazolinyl iminoquinoline ligand and its cobalt complex were designed and synthesized to control the establishment of tertiary or quaternary carbon centers at a remote position. This protocol is operationally simple, and a model for the stereochemical outcome has been proposed.

Automated summary

A cobalt-catalyzed desymmetrizing isomerization of exocyclic alkenes to generate chiral 1-methylcyclohexene derivatives with good yields and enantioselectivities was reported. A novel chiral thiazolinyl iminoquinoline ligand and its cobalt complex were designed and synthesized to control the establishment of tertiary or quaternary carbon centers at a remote position. This protocol is operationally simple, and a model for the stereochemical outcome has been proposed.