Catalytic Dehydrogenative β-Alkylation of Amino Acid Schiff Bases with Hydrocarbon

A synthetic method for the synthesis of a highly congested alpha,beta-dehydroamino acid through the beta-C-H bond activation of an amino acid Schiff base is described. Abundant hydrocarbon feedstock could be used as an alkylating reagent to afford an alpha,beta-dehydroamino acid bearing a quaternary carbon at the gamma-position with an exclusively (Z)-geometry. Notably, a tetrasubstituted olefin could be constructed from saturated starting materials. The transformation of the synthesized alpha,beta-dehydroamino acid into unnatural alpha-amino acid derivatives was also demonstrated.

Automated summary

This method involves the synthesis of a highly congested alpha,beta-dehydroamino acid through the beta-C-H bond activation of an amino acid Schiff base, with the use of abundant hydrocarbon feedstock as an alkylating reagent. The resulting alpha,beta-dehydroamino acid bears a quaternary carbon at the gamma-position with an exclusively (Z)-geometry. Additionally, a tetrasubstituted olefin can be constructed from saturated starting materials, and the synthesis also allows for the transformation into unnatural alpha-amino acid derivatives.