78605-38-6Relevant articles and documents
HIGHLY EFFICIENT OXAZOLONE-DERIVED REAGENTS FOR BETA-LACTAM FORMATION FROM BETA-AMINO ACIDS
Kunieda, Takehisa,Nagamatsu, Tomohisa,Higuchi, Tsunehiko,Hirobe, Masaaki
, p. 2203 - 2206 (2007/10/02)
Based on a unique leaving ability of 2-oxazolone moiety, highly efficient reagents have been developed for the formation of β-lactam compounds from β-amino acids including a facile preparation of penam, a basic skeleton of penicillins.
ACTIVATION OF CARBOXYL GROUPS BY DIPHENYL 2-OXO-3-OXAZOLINYLPHOSPHONATE. FACILE PREPARATION OF VERSATILE REAGENTS, 3-ACYL-2-OXAZOLONES
Kunieda, Takehisa,Higuchi, Tsunehiko,Abe, Yoshihiro,Hirobe, Masaaki
, p. 3253 - 3260 (2007/10/02)
Synthetic utility of the 2-oxazolone moiety as an excellent new leaving group is described.Based on such a function of the heterocycles, diphenyl 2-oxo-3-oxazolinylphosphonate has been newly introduced as a carboxyl-activating reagent which permits a facile direct preparation of 3-acyl-2-oxazolones and amides including peptides from a wide variety of carboxylic acids.The 3-acyl-2-oxazolides also serve as versatile reactive agents for highly chemoselective acyl-transfer to the nucleophilic species such as amines, alcohols and thiols, providing convenient and high-yield routes to amides, esters and thiol esters under mild conditions.They are also useful intermediates for ketones and alcohols.