Cobalt-Catalyzed Oxidative Phosphonylation of α-Amino Acid Derivatives and α-Amino Ketones for α-Aminophosphonates

Abstract

A novel and efficient direct oxidative phosphonylation of α-amino ketones and α-amino acid derivatives with dialkyl phosphites by the catalysis of a cobalt salt under air is disclosed. A variety of α-amino ketones and α-amino acid derivatives underwent the reaction well with dialkyl phosphites to produce the desired α-aminophosphonates. This protocol not only provides an alternative synthetic route for the preparation of diverse α-aminophosphonates but also avoids the use of potentially explosive peroxide agents.

Recent Advances in C(sp3)—H Phosphorylation Based on Secondary Phosphine Oxides and Phosphite Esters

“…A similar transformation for allylamines was then achieved by the group of Cheng (Entry 4). [57] The group of Zhu and Le [58] described a direct phosphorylation of α-amino ketones and α-amino acid derivatives with dialkyl phosphites catalyzed by a cobalt salt (Entry 5). Most recently, the group of Cheng and Ding [59] reported a simple approach for an electrochemical C(sp 3 )-H phosphorylation of secondary amines including unprotected THIQs with dialkyl phosphhites.…”

Visible‐Light‐Driven Redox Neutral Direct C−H Amination of Glycine Derivatives and Peptides with N‐Acyloxyphthalimides

“…Direct C(sp 3 )‐H functionalization of glycine derivatives or peptides containing glycine residues for acquiring unnatural amino acids or corresponding peptides has made tremendous achievements in the past few years. An array of synthetic strategies, including alkylation, [7a–g] arylation, alkynylation, alkenylation [7j] and phosphorylation [7h–i] have been developed (Scheme 1a). However, direct C−H amination of glycine and peptides with glycine residues has rarely been explored.…”

Thiocyanation of α-amino carbonyl compounds for the synthesis of aromatic thiocyanates

“…Besides, amoxicillin and clopidogrel demonstrate the application of αamino carbonyl compounds in medicine and provide resistance to some diseases. α-Amino carbonyl compounds are involved in many reactions, the most important among which are the reactions with nucleophiles, which include alcohols, 15 thiols, 15 amines, 16,17 phosphites, 18,19 nitromethane, 20 ketones, 21 1,3-dicarbonyl compounds, [22][23][24] (hetero) arenes, [25][26][27][28][29][30][31] and others.…”