Rhodium-catalyzed synthesis of 3-hydroxy-beta-lactams via oxonium ylide generation: three-component reaction between azetidine-2,3-diones, ethyl diazoacetate, and alcohols.
3-Substituted-3-hydroxy-beta-lactams, with two new adjacent stereogenic centers, have been prepared in a single step by a rhodium-catalyzed, three-component reaction between azetidine-2,3-diones, ethyl diazoacetate, and alcohols. Good to moderate stereoselectivity was obtained depending on the alcohol used. The stereochemistry of the new centers has been undoubtedly assigned by single crystal X-ray diffraction.
Alcaide
Benito
B
Departamento de Química Orgánica I, Facultad de Química, Universidad Complutense, 28040-Madrid, Spain. alcaideb@quim.ucm.es
Almendros
Pedro
P
Aragoncillo
Cristina
C
Callejo
Ricardo
R
Ruiz
M Pilar
MP
Torres
M Rosario
MR
D000438:Alcohols / Q000737:chemistry*; D001384:Azetidines / Q000737:chemistry*; D002384:Catalysis; D003979:Diazonium Compounds / Q000737:chemistry*; D007769:Lactams / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D012238:Rhodium / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization
D000438:Alcohols; D001384:Azetidines; D003979:Diazonium Compounds; D007769:Lactams; D012238:Rhodium; C032111:diazoacetic ester