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Synthesis 2005(4): 530-536  
DOI: 10.1055/s-2004-837304
PAPER
© Georg Thieme Verlag Stuttgart · New York

Liquid-Phase Syntheses of 2,3-Dihydro-4-pyridones and β-Lactams from PEG-Supported Aldehydes

Wang-Ge Shou, Yun-Yun Yang, Yan-Guang Wang*
Department of Chemistry, Zhejiang University, Hangzhou 310027, P. R. China
Fax: +86(571)87951512; e-Mail: orgwyg@zju.edu.cn;
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Publication History

Received 13 September 2004
Publication Date:
22 December 2004 (online)

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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