Regioselective Synthesis of Tetrasubstituted Olefins via an Alkenyl Catellani Reaction
Modular and Regioselective Synthesis of All-Carbon Tetrasubstituted Olefins Enabled by an Alkenyl Catellani Reaction.
Nat. Chem. 2019;
21 January 2020 (online)
The Dong group reports a general method for the bis-functionalization of alkenes via a Catellani reaction. This method affords unsymmetrical tetrasubstituted alkenes. The use of a functionalized norbornene gave high yields and selectivities.
Utilization of the N-methyl amide-substituted norbornene (N11) was optimal as it gave the highest yield of product and eliminated the formation of the cyclopropane adduct. A mechanism was proposed that was supported with detailed kinetic analysis.