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题名: Do reaction conditions affect the stereoselectivity in the Staudinger reaction?
作者: Wang, Yikai;  Liang, Yong;  Jiao, Lei;  Du, Da-Ming;  Xu, Jiaxi
刊名: JOURNAL OF ORGANIC CHEMISTRY
发表日期: 2006-09-01
DOI: 10.1021/jo0611521
卷: 71, 期:18, 页:6983-6990
收录类别: SCI ;  IC
文章类型: Article
WOS标题词: Science & Technology ;  Physical Sciences
类目[WOS]: Chemistry, Organic
研究领域[WOS]: Chemistry
英文摘要: The stereochemistry is one of the critical issues in the Staudinger reaction. We have proposed the origin of the stereoselectivity recently. The effects of solvents, additives, and pathways of ketene generation on the stereoselectivity were investigated by using a clean Staudinger reaction, which is a sensitive reaction system to the stereoselectivity. The results indicate that the additives, usually existed and generated in the Staudinger reaction, and the pathways of the ketene generation do not generally affect the stereoselectivity. The solvent affects the stereoselectivity. The polar solvent is favorable to the formation of trans-beta-lactams. The addition orders of the reagents affect the stereoselectivity in the Staudinger reaction between acyl chlorides and imines. The addition of a tertiary amine into a solution of the acyl chloride and the imine generally decreases the stereoselectivity, which is affected by the interval between additions of the acyl chloride and the tertiary amine, and the imine substituents. Our current results provide further understanding on the stereochemistry of the Staudinger reaction between acyl chlorides and imines and on the factors affecting the stereochemistry and also provide a method to prepare beta-lactams with the desired relative configuration via rationally tuning the stereoselectivity-controlling factors in the Staudinger reaction.
关键词[WOS]: CHROMIUM CARBENE COMPLEXES ;  BETA-LACTAM ANTIBIOTICS ;  IMINE CYCLOADDITION REACTION ;  ASYMMETRIC-SYNTHESIS ;  STEREOSPECIFIC SYNTHESIS ;  STEREOCONTROLLED SYNTHESIS ;  PHOTOLYTIC REACTION ;  BUILDING-BLOCKS ;  CYCLO-ADDITIONS ;  KETENES
语种: 英语
WOS记录号: WOS:000240020100034
Citation statistics: 
内容类型: 期刊论文
URI标识: http://cas-ir.dicp.ac.cn/handle/321008/140261
Appears in Collections:中国科学院大连化学物理研究所_期刊论文

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作者单位: 1.Peking Univ, Beijing Natl Lab Mol Sci, Key Lab Bioorgan Chem & Mol Engn, Minist Educ,Coll Chem & Mol Engn, Beijing 100871, Peoples R China

Recommended Citation:
Wang, Yikai,Liang, Yong,Jiao, Lei,et al. Do reaction conditions affect the stereoselectivity in the Staudinger reaction?[J]. JOURNAL OF ORGANIC CHEMISTRY,2006,71(18):6983-6990.
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