Kinetic resolution of substituted 1,3-4H-5,6-dihydrooxazines with carboxylesterase NP: synthesis of (3S,1'R)-3-(1'-hydroxyethyl)-azetidin-2-one.
The kinetic resolution of oxazinyl-ethyl carboxylates 4, is reported employing carboxylesterase NP as biocatalyst. Starting from the anti racemic stereoisomers 4c-d, the unreacted ester is obtained in 40% yield and 93% e.e. The enantiomeric acid is obtained in the open form. Cyclization of the latter and base equilibration allows recycling of the undesired stereoisomer. Compound 4d has the absolute configuration required in the azetidinone 3d, an intermediate in the synthesis of penems and carbapenems.
Fuganti
C
C
CNR, Centro per lo Studio delle Sostanze Organiche Naturali, Dipartimento di Chimica, Politecnico di Milano, Italy.
Lanati
S
S
Servi
S
S
D001384:Azetidines / Q000138:chemical synthesis* / Q000737:chemistry; D043182:Carboxylesterase; D002264:Carboxylic Acids / Q000737:chemistry* / Q000302:isolation & purification; D002265:Carboxylic Ester Hydrolases; D007700:Kinetics; D015394:Molecular Structure; D010078:Oxazines / Q000737:chemistry* / Q000302:isolation & purification; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
C092086:3-(1'-hydroxyethyl)azetidin-2-one; D001384:Azetidines; D002264:Carboxylic Acids; D010078:Oxazines; D002265:Carboxylic Ester Hydrolases; D043182:Carboxylesterase