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Synthesis of β-Lactams from 1-Citronellal

 

作者: S. Watanabe,   T. Fujita,   M. Sakamoto,   I. Shirakawa,   K. Sugahara,  

 

期刊: Journal of Essential Oil Research  （Taylor Available online 1992）
卷期: Volume 4, issue 6  

页码: 595-599

 

ISSN:1041-2905

 

年代: 1992

 

DOI:10.1080/10412905.1992.9698141

 

出版商: Taylor & Francis Group

 

关键词: Citronellal;N-[(3R)-3,7-dimethyl-6-octen-1-ylidene]-N-cyclohexylamine;β-lactam,4-[(2R)-2,6-dimethyl-5-hepten-l-yl]-(1-cyclohexyl)azetidin-2-one;Reformatsky reaction;N-[(3R)-3,7-dimethyl-1,6-octadien-1-yl]-N-cyclohexyl-2 methylpropionamide

 

数据来源: Taylor

 

摘要:

This paper concerns a preparative method of β-lactam formation using N-[(3R)-3, 7-dimethyl-6-octen-1-ylidene]-N-cyclohexylamine [I] derived from 1-citronellal. The reaction of [I] with ethyl bromoacetate in the presence of zinc gave a β-lactam 4-[(2R)-2, 6-dimethyl-5-hepten-1-yl]-(1-cyclohexyl)azetidin-2-one [II]. Instead of β-lactam for-mation, N-[(3R)-3, 7-dimethyl-1, 6-octadien-1-yl]-N-cyclohexyl-2-methylpropionamide[III] was obtained from the reaction of [I] with isobutyryl chloride and triethylamine.

 

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