Tin powder‐promoted oxidation/allylation of glycine esters: Synthesis ofγ,δ‐unsaturatedα‐amino acid esters

Abstract

An efficient tin powder-promoted oxidation/allylation reaction of glycine esters with allyl bromides is developed, which affords γ,δ-unsaturated α-amino acid esters under mild conditions without any other transition metal catalysts. This method avoids the use of unstable imine as starting material, and provides an efficient method for synthesis of γ,δ-unsaturated α-amino acid esters and α-methylene-γ-lactam derivatives.

Oxidation/Alkylation of Amino Acids with α-Bromo Carbonyls Catalyzed by Copper and Quick Access to HDAC Inhibitor

“…The reaction also exhibited high alkylation efficiency for secondary α-bromo esters (1, and 6−9). Notably, an 87% isolated yield was obtained for the substrates within closed rings (9). Finally, the primary and second αbromo ketones proved to be compatible, as evident in the products of 10-11.…”