Academic Journal
Spirocyclopropanation Reaction of para-Quinone Methides with Sulfonium Salts: The Synthesis of Spirocyclopropanyl para-Dienones
| العنوان: | Spirocyclopropanation Reaction of para-Quinone Methides with Sulfonium Salts: The Synthesis of Spirocyclopropanyl para-Dienones |
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| المؤلفون: | Zhang, Xiang-Zhi, Du, Ji-Yuan, Deng, Yu-Hua, Chu, Wen-Dao, Yan, Xu, Yu, Ke-Yin, Fan, Chun-An |
| المساهمون: | Fan, CA (reprint author), Lanzhou Univ, Coll Chem & Chem Engn, State Key Lab Appl Organ Chem, 222 Tianshui Nanlu, Lanzhou 730000, Peoples R China., Fan, CA (reprint author), Peking Univ, State Key Lab Nat & Biomimet Drugs, 38 Xueyuan Lu, Beijing 100191, Peoples R China., Lanzhou Univ, Coll Chem & Chem Engn, State Key Lab Appl Organ Chem, 222 Tianshui Nanlu, Lanzhou 730000, Peoples R China., Peking Univ, State Key Lab Nat & Biomimet Drugs, 38 Xueyuan Lu, Beijing 100191, Peoples R China., Chinese Acad Sci, Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China. |
| المصدر: | SCI |
| بيانات النشر: | JOURNAL OF ORGANIC CHEMISTRY |
| سنة النشر: | 2016 |
| المجموعة: | Peking University Institutional Repository (PKU IR) / 北京大学机构知识库 |
| مصطلحات موضوعية: | ASYMMETRIC 1,6-CONJUGATE ADDITION, FORMAL 4+1 ANNULATION, STABLE SULFUR YLIDES, BENZOQUINONE METHIDE, EXPEDIENT ACCESS, IN-SITU, CYCLOADDITION, NITROOLEFINS, POLYMERS, ACID |
| الوصف: | A novel DBU-mediated stereoselective spirocyclopropanation of para-quinone methides with sulfonium salts has been developed on the basis of the mode involving a 1,6-conjugate addition/intramolecular dearomatizing cyclization cascade. This reaction provides a mild and effective method for the assembly of synthetically and structurally interesting spirocyclopropanyl para-dienones. The feasibility for the enantioselective access to such functionalized para-dienones has also been explored by using the axially chiral sulfonium salt. Importantly, the regioselective ring openings of the related spirocyclopropanyl para-dienones have been achieved divergently. ; National Natural Science Foundation of China [21572083, 21322201, 21290180]; Fundamental Research Funds for the Central Universities [lzujbky-2015-48, lzujbky-2013-ct02]; State Key Laboratory of Natural and Biomimetic Drugs [K20150213]; PCSIRT [IRT_15R28]; 111 Project of Ministry of Education of China [111-2-17]; Chang Jiang Scholars Program ; SCI(E) ; ARTICLE ; fanchunan@lzu.edu.cn ; 6 ; 2598-2606 ; 81 |
| نوع الوثيقة: | journal/newspaper |
| اللغة: | English |
| تدمد: | 0022-3263 |
| Relation: | JOURNAL OF ORGANIC CHEMISTRY.2016,81,(6),2598-2606.; 1397370; http://hdl.handle.net/20.500.11897/438434; WOS:000372664700038 |
| DOI: | 10.1021/acs.joc.5b02725 |
| الاتاحة: | https://hdl.handle.net/20.500.11897/438434 https://doi.org/10.1021/acs.joc.5b02725 |
| رقم الانضمام: | edsbas.452C2DD2 |
| قاعدة البيانات: | BASE |
| تدمد: | 00223263 |
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| DOI: | 10.1021/acs.joc.5b02725 |