Osmium-catalyzed oxidation of β-lactams with peroxides

β2‐amino acids—syntheses, occurrence in natural products, and components of β‐peptides1,2

“…The resulting syn-(2S,3R)-␤ 2 -homothreonine derivative is obtained with optimal diastereo-and enantioselectivities, making use of several chiral complexes, [192][193][194][195][196][197] and can be transformed to the ␤-lactam key intermediate of carbapenem antibiotics. 198,199 Another example of a catalytic enantioselective reaction for the preparation of ␤ 2 -amino acids was reported by Davies and Venkataramani. 200 The crucial reaction is an asymmetric C-H activation of NBoc-protected methylamines by means of a [Rh 2 ((S)-DOSP) 4 …”

Ruthenium‐Catalyzed Oxidation for Organic Synthesis

“…(7.71)) [118]. Aerobic oxidation of b-lactams can be performed highly efficiently in the presence of acetaldehyde, an acid, and sodium acetate [119]. Typically, the RuCl 3 -catalyzed oxidation of b-lactam 54 with molecular oxygen (1 atm) in the presence of acetaldehyde and sodium carboxylate gave the corresponding 4-acyloxy b-lactam 55 in 91% yields (de >99%) (Eq.…”

“…Oxo-metal species can be generated by the reaction of a low valent ruthenium complex with molecular oxygen in the presence of an aldehyde [119]. Thus, the ruthenium-catalyzed oxidation of alkanes with molecular oxygen in the presence of acetaldehyde gives alcohols and ketones efficiently [139a].…”

Transition Metal Catalysis in the Baeyer-Villiger Oxidation of Ketones

“…report followed some earlier patents by, among others, Union Carbide, and Mitsubishi Kasei, [43] and exploits the easy autoxidation of aldehydes to promote the in situ formation of peroxy acids. This system has been highly successful in the promotion of the aerobic oxidation of a variety of substrates including olefins, [44] aldehydes, [45] silyl enolethers, [46] lactams, [47] and alkanes, [48] and has proved useful for the Baeyer ± Villiger oxidation of ketones as well.…”