Diastereoselectivity enhancement in the 1,3-cycloaddition of beta-lactam aldehydes. Application to the synthesis of enantiopure indolizidinone amino esters.
[reaction: see text] Enantiopure alpha-alkoxy beta-lactam acetaldehydes were prepared via the thiazole-based one-carbon homologation. The 1,3-dipolar cycloaddition reaction involving alpha-alkoxy beta-lactam acetaldehyde-derived azomethine ylides gave with excellent diastereoselectivity highly functionalized 2-azetidinone-tethered prolines, which were directly used for the first preparation of azabicyclo[4.3.0]nonane (indolizidinone) amino esters from beta-lactams.
Alcaide
Benito
B
Departamento de Química Orgánica I, Facultad de Química, Universidad Complutense de Madrid, Spain. alcaideb@quim.ucm.es
Almendros
Pedro
P
Redondo
María C
MC
Ruiz
M Pilar
MP
D000085:Acetates / Q000737:chemistry; D000447:Aldehydes / Q000737:chemistry*; D000586:Amination; D001391:Azo Compounds / Q000737:chemistry; D004952:Esters / Q000138:chemical synthesis / Q000737:chemistry*; D007211:Indoles / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D018030:Silver Compounds / Q000737:chemistry; D013237:Stereoisomerism; D047090:beta-Lactams / Q000737:chemistry*
D000085:Acetates; D000447:Aldehydes; D001391:Azo Compounds; D004952:Esters; D007211:Indoles; D018030:Silver Compounds; D047090:beta-Lactams; C103100:silver acetate