577974-10-8Relevant articles and documents
Synthesis of γ-Oxo-α-amino Acids via Radical Acylation with Carboxylic Acids
Merkens, Kay,Aguilar Troyano, Francisco José,Anwar, Khadijah,Gómez-Suárez, Adrián
, p. 8448 - 8456 (2021)
Herein we present a highly efficient, light-mediated, deoxygenative protocol to access γ-oxo-α-amino acid derivatives. This radical methodology employs photoredox catalysis, in combination with triphenylphosphine, to generate acyl radicals from readily available (hetero)aromatic and vinylic carboxylic acids. This approach allows for the straightforward synthesis of γ-oxo-α-amino acids bearing a wide range of functional groups (e.g., Cl, CN, furan, thiophene, Bpin) in synthetically useful yields (～60% average yield). To further highlight the utility of the methodology, several deprotection and derivatization reactions were carried out.
Catalytic, asymmetric Mannich-type reactions of α-imino esters bearing readily removable substituents on nitrogen
Nakamura, Yoshitaka,Matsubara, Ryosuke,Kiyohara, Hiroshi,Kobayashi, Shu
, p. 2481 - 2484 (2007/10/03)
(Matrix presented) Catalytic, enantioselective Mannich-type reactions of α-imino esters bearing readily removable substituents on nitrogen are described. Several N-carbamate-protected α-imino esters, which are readily prepared from 2-bromoglycine esters using a polymer-supported amine, reacted with silicon enolates to afford the desired adducts in high yields with high enantioselectivity using a copper(II)-diamine complex. Easy deprotection of the product amine and transformation to free o-amino acid derivatives have also been demonstrated.
