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题名: Mechanisms of Cascade Reactions in the Syntheses of Camptothecin-Family Alkaloids: Intramolecular [4(+)+2] Reactions of N-Arylimidates and Alkynes
作者: Liang, Yong1;  Jiang, Xing1;  Yu, Zhi-Xiang1
刊名: ORGANIC LETTERS
发表日期: 2009-11-19
DOI: 10.1021/ol902260a
卷: 11, 期:22, 页:5302-5305
收录类别: SCI
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 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.
关键词[WOS]: DIELS-ALDER REACTIONS ;  CYCLOADDITION REACTIONS ;  MOLECULAR MECHANISM ;  TRIFLUOROMETHANESULFONATE ;  CYCLOPENTADIENE ;  DERIVATIVES ;  CYCLIZATION ;  EFFICIENT ;  ENERGIES ;  STRATEGY
语种: 英语
WOS记录号: WOS:000271583000053
Citation statistics: 
内容类型: 期刊论文
URI标识: http://cas-ir.dicp.ac.cn/handle/321008/141258
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, Coll Chem, Key Lab Bioorgan Chem & Mol Engn, Beijing Natl Lab Mol Sci,Minist Educ, Beijing 100871, Peoples R China

Recommended Citation:
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.
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