ICCAS OpenIR
Cascade reaction of beta,gamma-unsaturated alpha-ketoesters with phenols in trityl chloride/TFA system. Highly selective synthesis of 4-aryl-2H-chromenes and their applications
Wu, Yan-Chao; Li, Hui-Jing; Liu, Li; Liu, Zhe; Wang, Dong; Chen, Yong-Jun
2011
Source PublicationORGANIC & BIOMOLECULAR CHEMISTRY
ISSN1477-0520
Volume9Issue:8Pages:2868-2877
AbstractThe treatment of beta,gamma-unsaturated alpha-ketoesters with phenols in the presence of trityl chloride and 4 angstrom molecular sieves in refluxing trifluoroacetic acid afforded 4-aryl-2H-chromenes in high yields, in which a reverse of the regiochemistry of Jorgensen-Rutjes chromane synthesis was observed. The isolation of 4H-chromene intermediates, confirmed by single-crystal X-ray analysis, indicates that the early stage of the reaction involves a Friedel-Crafts alkylation/cyclodehydration processes. Stirring of the 4H-chromene intermediate with trityl chloride in deuterotrifluoroacetic acid under reflux afforded the 2H-chromene and triphenylmethane in high yields, which implies the late stage of the reaction involves a hydrogen transfer process. Highly selective derivation of the hydroxyl esters to the corresponding hydroxyl amides, amino acids, amino esters and Friedel-Crafts adducts was further accomplished. Our endeavors will lead to a better understanding of the controlling elements behind their structural motifs. The products were confirmed unambiguously from their spectra and by single-crystal X-ray analysis.
DOI10.1039/c0ob01143f
Indexed BySCI ; IC ; CCR
Language英语
WOS IDWOS:000288904500039
PublisherROYAL SOC CHEMISTRY
Citation statistics
Cited Times:19[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.iccas.ac.cn/handle/121111/73550
Collection中国科学院化学研究所
Corresponding AuthorWu, Yan-Chao
AffiliationChinese Acad Sci, Inst Chem, CAS Key Lab Mol Recognit & Funct, BNLMS, Beijing 100190, Peoples R China
Recommended Citation
GB/T 7714
Wu, Yan-Chao,Li, Hui-Jing,Liu, Li,et al. Cascade reaction of beta,gamma-unsaturated alpha-ketoesters with phenols in trityl chloride/TFA system. Highly selective synthesis of 4-aryl-2H-chromenes and their applications[J]. ORGANIC & BIOMOLECULAR CHEMISTRY,2011,9(8):2868-2877.
APA Wu, Yan-Chao,Li, Hui-Jing,Liu, Li,Liu, Zhe,Wang, Dong,&Chen, Yong-Jun.(2011).Cascade reaction of beta,gamma-unsaturated alpha-ketoesters with phenols in trityl chloride/TFA system. Highly selective synthesis of 4-aryl-2H-chromenes and their applications.ORGANIC & BIOMOLECULAR CHEMISTRY,9(8),2868-2877.
MLA Wu, Yan-Chao,et al."Cascade reaction of beta,gamma-unsaturated alpha-ketoesters with phenols in trityl chloride/TFA system. Highly selective synthesis of 4-aryl-2H-chromenes and their applications".ORGANIC & BIOMOLECULAR CHEMISTRY 9.8(2011):2868-2877.
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