Lewis-Acid-Catalysed Tandem Meinwald Rearrangement/Intermolecular [3+2]-Cycloaddition of Epoxides with Donor-Acceptor Cyclopropanes: Synthesis of Functionalized Tetrahydrofurans

Pandey Ashok Kumar; Ghosh Asit; Banerjee Prabal

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Lewis-Acid-Catalysed Tandem Meinwald Rearrangement/Intermolecular [3+2]-Cycloaddition of Epoxides with Donor-Acceptor Cyclopropanes: Synthesis of Functionalized Tetrahydrofurans

机译：Lewis酸催化的串联Meinwald重排/分子间[3 + 2]-环氧化物与供体-受体环丙烷的环加成反应：功能化四氢呋喃的合成

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摘要

A Lewis-acid-catalysed tandem Meinwald rearrangement/[3+2]-cycloaddition of epoxides with donor-acceptor cyclopropanes to synthesize varieties of cis-2,5-aryl-benzyl-substituted tetrahydrofurans is described. An enantioselective version of the same transformation was achieved using an InCl3-PyBOX catalyst system.

机译：描述了路易斯酸催化的串联的梅恩瓦尔德重排/环氧化物与供体-受体环丙烷的[3 + 2]-环加成反应，以合成各种顺式2,5-芳基-苄基取代的四氢呋喃。使用InCl3-PyBOX催化剂系统可实现相同转化的对映选择性。

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《European journal of organic chemistry》 |2015年第11期|共7页
作者
Pandey Ashok Kumar; Ghosh Asit; Banerjee Prabal;
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正文语种 eng
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Asymmetric synthesis; Cyclization; Oxygen heterocycles; Small ring systems; Epoxides;

机译：不对称合成环化氧杂环小环系统环氧;

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1. Lewis-Acid-Catalysed Tandem Meinwald Rearrangement/Intermolecular [3+2]-Cycloaddition of Epoxides with Donor-Acceptor Cyclopropanes: Synthesis of Functionalized Tetrahydrofurans [J] . Pandey Ashok Kumar, Ghosh Asit, Banerjee Prabal European journal of organic chemistry . 2015,第11期

机译：Lewis酸催化的串联Meinwald重排/分子间[3 + 2]-环氧化物与供体-受体环丙烷的环加成反应：功能化四氢呋喃的合成
2. Construction of fused- and spiro-oxa-[n.2.1] skeletons by a tandem epoxide rearrangement/ intramolecular [3+2] cycloaddition of cyclopropanes with carbonyls [J] . Lu-Feng Wang, Zi-Fa Shi, Xiao-Ping Cao, Chemical Communications . 2014,第59期

机译：通过串联环氧化物重排/环丙烷与羰基的分子内[3 + 2]环加成反应构建熔融和螺氧基-[n.2.1]骨架
3. Novel synthesis of highly functionalized cyclopentane derivatives via [3+2] cycloaddition reactions of donor-acceptor cyclopropanes and (E)-3-aryl-2-cyanoacrylates [J] . Dai Chenlu, Li Mingshuang, Chen Mengjun, Journal of chemical research: reviews and research papers from all branches of chemistry . 2019,第1a2期

机译：通过[3 + 2]循环加油反应的新型官能化环戊烷衍生物的新的合成供体 - 受体环烷基和（e）-3-芳基-2-氰基丙烯酸丙烯酸酯
4. High Pressure Promoted 4+2/3+2 Tandem Cycloadditions of Nitrostyrene and Enol Ethers [C] . G.J.T.Kuster, F.Kalmoua, J.W.Scheeren Joint meeting of the European High Pressure Research Group and Food Chemistry Group of The Royal Society of Chemistry on high pressure food science, bioscience and chemistry . 1998

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5. I. Addition of arylhalocarbenes to vinyl isocyanates II. Synthesis of highly functionalized dihydro- and tetrahydrofuran derivates via [3+2] cycloaddition III. Synthesis of benzoxepines. [D] . Aasmul, Mona. 2002

机译：I.芳基卤代卡宾加成到异氰酸乙烯基酯上II。经由[3 + 2]环加成反应III合成高度官能化的二氢和四氢呋喃衍生物。苯并x庚因的合成。
6. Transition-Metal-Free 3+2 Dehydration Cycloaddition of Donor-Acceptor Cyclopropanes With 2-Naphthols [O] . Hua Zhao, Peng Shen, Dongru Sun, 2021

机译：无过渡金属3 + 2脱水环加成供体 - 受体环丙烯酸环加入2-萘酚
7. FERROCENYL-SUBSTITUTED TETRAHYDROTHIOPHENES VIA FORMAL (3+2)-CYCLOADDITION REACTIONS OF FERROCENYL THIOKETONES WITH DONOR-ACCEPTOR CYCLOPROPANES [O] . Grzegorz Mloston, Mateusz Kowalczyk, André U Augustin, 2020

机译：用富钴硫基硫代酮与供体 - 受体环丙烷转移反应的亚茂铁烯基取代的四氢噻吩

Lewis-Acid-Catalysed Tandem Meinwald Rearrangement/Intermolecular [3+2]-Cycloaddition of Epoxides with Donor-Acceptor Cyclopropanes: Synthesis of Functionalized Tetrahydrofurans

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