I2-Catalyzed enantioselective ring expansion of beta-lactams to gamma-lactams through a novel C3-C4 bond cleavage. Direct entry to protected 3,4-dihydroxypyrrolidin-2-one derivatives.
Molecular iodine (10 mol%) efficiently catalyzes the ring expansion of 4-oxoazetidine-2-carbaldehydes in the presence of tert-butyldimethyl cyanide to afford protected 5-cyano-3,4-dihydroxypyrrolidin-2-ones with good yield and high diastereoselectivity, through a novel C3-C4 bond cleavage of the beta-lactam nucleus.
Alcaide
Benito
B
Departamento de Química Orgánica, Facultad de Química, Universidad Complutense de Madrid, 28040-Madrid, Spain. alcaideb@quim.ucm.es
Almendros
Pedro
P
Cabrero
Gema
G
Ruiz
M Pilar
MP
D000447:Aldehydes / Q000737:chemistry; D002384:Catalysis; D007455:Iodine / Q000737:chemistry*; D007769:Lactams / Q000138:chemical synthesis* / Q000737:chemistry*; D008968:Molecular Conformation; D011760:Pyrrolidinones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
C508205:3,4-dihydroxypyrrolidin-2-one; D000447:Aldehydes; D007769:Lactams; D011760:Pyrrolidinones; D007455:Iodine