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Mechanisms of Cascade Reactions in the Syntheses of Camptothecin-Family Alkaloids: Intramolecular [4(+)+2] Reactions of N-Arylimidates and Alkynes
Liang, Yong; Jiang, Xing; Yu, Zhi-Xiang
Source PublicationORGANIC LETTERS
2009-11-19
DOI10.1021/ol902260a
Volume11Issue:22Pages:5302-5305
Indexed BySCI
SubtypeArticle
WOS HeadingsScience & Technology ; Physical Sciences
WOS SubjectChemistry, Organic
WOS Research AreaChemistry
WOS KeywordDIELS-ALDER REACTIONS ; CYCLOADDITION REACTIONS ; MOLECULAR MECHANISM ; TRIFLUOROMETHANESULFONATE ; CYCLOPENTADIENE ; DERIVATIVES ; CYCLIZATION ; EFFICIENT ; ENERGIES ; STRATEGY
AbstractThe key steps of cascade reactions employed In the syntheses of camptothecin-family alkaloids by Fortunak and Yao are intramolecular aza-Diels-Alder (IADA) reactions between in situ generated N-arylimidates and alkynes. The efficiencies of the IADA reactions are different but not well-understood. DFT calculations shown here provide insights Into these two IADA reactions and well-rationalize why hexaphenyloxodiphosphonium triflate (Hendrickson reagent) as an amide-activating reagent Is superior to trimethyloxonium fluoroborate.
Language英语
WOS IDWOS:000271583000053
Citation statistics
Cited Times:22[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://cas-ir.dicp.ac.cn/handle/321008/141258
Collection中国科学院大连化学物理研究所
AffiliationPeking Univ, Coll Chem, Key Lab Bioorgan Chem & Mol Engn, Beijing Natl Lab Mol Sci,Minist Educ, Beijing 100871, Peoples R China
Recommended Citation
GB/T 7714
Liang, Yong,Jiang, Xing,Yu, Zhi-Xiang. Mechanisms of Cascade Reactions in the Syntheses of Camptothecin-Family Alkaloids: Intramolecular [4(+)+2] Reactions of N-Arylimidates and Alkynes[J]. ORGANIC LETTERS,2009,11(22):5302-5305.
APA Liang, Yong,Jiang, Xing,&Yu, Zhi-Xiang.(2009).Mechanisms of Cascade Reactions in the Syntheses of Camptothecin-Family Alkaloids: Intramolecular [4(+)+2] Reactions of N-Arylimidates and Alkynes.ORGANIC LETTERS,11(22),5302-5305.
MLA Liang, Yong,et al."Mechanisms of Cascade Reactions in the Syntheses of Camptothecin-Family Alkaloids: Intramolecular [4(+)+2] Reactions of N-Arylimidates and Alkynes".ORGANIC LETTERS 11.22(2009):5302-5305.
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