ICCAS OpenIR
Reversal of nucleophilicity of enamides in water: Control of cyclization pathways by reaction media for the orthogonal synthesis of dihydropyridinone and pyrrolidinone Clausena alkaloids
Yang, Luo; Zheng, Qi-Yu; Wang, De-Xian; Huang, Zhi-Tang; Wang, Mei-Xiang
2008-06-19
Source PublicationORGANIC LETTERS
ISSN1523-7060
Volume10Issue:12Pages:2461-2464
AbstractA highly efficient, metal-free, and divergent method for the synthesis of 3,4-dihydropyridin-2-one and pyrrolidin-2-one Clausena alkaloids and their analogs is reported. While the oxirane-containing enamides underwent the TFA-mediated 6-endo-enamide-epoxide cyclization reaction in Bu(t)OH to produce homoclausenamides, an unprecedented nucleophilic reaction occurred at the alpha-carbon of enamides in water to yield 5-endo-enamide-epoxide cyclization products in excellent yields. The reversal of nucleophilicity of enamides in intramolecular cyclization is discussed in terms of steric and electronic effects of the oxirane-containing enamides.
DOI10.1021/ol800740h
Indexed BySCI ; IC ; CCR
Language英语
WOS IDWOS:000256762100034
PublisherAMER CHEMICAL SOC
Citation statistics
Cited Times:54[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.iccas.ac.cn/handle/121111/63218
Collection中国科学院化学研究所
Corresponding AuthorWang, Mei-Xiang
AffiliationChinese Acad Sci, Beijing Natl Lab Mol Sci, Inst Chem, Biol Chem Lab, Beijing 100190, Peoples R China
Recommended Citation
GB/T 7714
Yang, Luo,Zheng, Qi-Yu,Wang, De-Xian,et al. Reversal of nucleophilicity of enamides in water: Control of cyclization pathways by reaction media for the orthogonal synthesis of dihydropyridinone and pyrrolidinone Clausena alkaloids[J]. ORGANIC LETTERS,2008,10(12):2461-2464.
APA Yang, Luo,Zheng, Qi-Yu,Wang, De-Xian,Huang, Zhi-Tang,&Wang, Mei-Xiang.(2008).Reversal of nucleophilicity of enamides in water: Control of cyclization pathways by reaction media for the orthogonal synthesis of dihydropyridinone and pyrrolidinone Clausena alkaloids.ORGANIC LETTERS,10(12),2461-2464.
MLA Yang, Luo,et al."Reversal of nucleophilicity of enamides in water: Control of cyclization pathways by reaction media for the orthogonal synthesis of dihydropyridinone and pyrrolidinone Clausena alkaloids".ORGANIC LETTERS 10.12(2008):2461-2464.
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