Spirocyclopropanation Reaction of para-Quinone Methides with Sulfonium Salts: The Synthesis of Spirocyclopropanyl para-Dienones | |
Department | OSSO国家重点实验室 |
Zhang, Xiang-Zhi1; Du, Ji-Yuan1; Deng, Yu-Hua3; Chu, Wen-Dao1; Yan, Xu1; Yu, Ke-Yin1; Fan, Chun-An1,2 | |
2016 | |
Source Publication | Journal of Organic Chemistry
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ISSN | 0022-3263 |
Volume | 81Issue:6Pages:2598-2606 |
Abstract | 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. |
Subject Area | 物理化学与绿色催化 |
DOI | 10.1021/acs.joc.5b02725 |
Funding Organization | the National Natural Science Foundation of China (21572083;21322201;21290180);the Fundamental Research Funds for the Central Universities (lzujbky-2015-48;lzujbky-2013-ct02);the State Key Laboratory of Natural and Biomimetic Drugs (K20150213);PCSIRT (IRT-15R28);the 111 Project of Ministry of Education of China (111-2-17);Changjiang Scholars Program (C.-A.F.) |
Indexed By | SCI |
If | 4.849 |
Language | 英语 |
compositor | 第三作者单位 |
Citation statistics | |
Document Type | 期刊论文 |
Identifier | http://ir.licp.cn/handle/362003/19987 |
Collection | 羰基合成与选择氧化国家重点实验室(OSSO) |
Corresponding Author | Fan, Chun-An |
Affiliation | 1.Lanzhou Univ, Coll Chem & Chem Engn, State Key Lab Appl Organ Chem, 222 Tianshui Nanlu, Lanzhou 730000, Peoples R China 2.Peking Univ, State Key Lab Nat & Biomimet Drugs, 38 Xueyuan Lu, Beijing 100191, Peoples R China 3.Chinese Acad Sci, Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China |
Recommended Citation GB/T 7714 | Zhang, Xiang-Zhi,Du, Ji-Yuan,Deng, Yu-Hua,et al. Spirocyclopropanation Reaction of para-Quinone Methides with Sulfonium Salts: The Synthesis of Spirocyclopropanyl para-Dienones[J]. Journal of Organic Chemistry,2016,81(6):2598-2606. |
APA | Zhang, Xiang-Zhi.,Du, Ji-Yuan.,Deng, Yu-Hua.,Chu, Wen-Dao.,Yan, Xu.,...&Fan, Chun-An.(2016).Spirocyclopropanation Reaction of para-Quinone Methides with Sulfonium Salts: The Synthesis of Spirocyclopropanyl para-Dienones.Journal of Organic Chemistry,81(6),2598-2606. |
MLA | Zhang, Xiang-Zhi,et al."Spirocyclopropanation Reaction of para-Quinone Methides with Sulfonium Salts: The Synthesis of Spirocyclopropanyl para-Dienones".Journal of Organic Chemistry 81.6(2016):2598-2606. |
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