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DOI: 10.1055/s-2004-837304
Liquid-Phase Syntheses of 2,3-Dihydro-4-pyridones and β-Lactams from PEG-Supported Aldehydes
Publication History
Publication Date:
22 December 2004 (online)

Abstract
General and efficient methods for the construction of 2,3-dihydro-4-pyridones and β-lactams on soluble polymer support have been developed. The aza-Diels-Alder reaction of Danishefsky’s diene with poly(ethylene glycol) (PEG)-bound imines derived from PEG-bound aldehydes, followed by cleavage from the support, afforded 2, 3-dihydro-4-pyridones. On the other hand, the Staudinger reaction of PEG-bound imines with ketenes generated in situ from acid chlorides, followed by cleavage from the PEG, gave cis-β-lactams. The products were obtained in good yields and purities.
Key Words
poly(ethylene glycol) (PEG) - 2 - 3-dihydro-4-pyridones - aza-Diels-Alder reaction - β-lactams - cycloaddition - liquid-phase synthesis
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