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研究生： 柳彥成
Liou, Yan-Cheng
論文名稱： (一) 使用鄰羥基對亞甲基苯醌經由 1,6-膦加成/氧-醯化/威悌反應建構官能化苯并呋喃衍生物 (二) 膦催化之化學選擇性還原/亞硝酸離去/威悌反應建構 3-烯基苯并呋喃衍生物 (三) 亞烷基米氏酸與亞胺葉立德經 (3+2) 環加成/內酯化反應合成高鏡像選擇性之𠳭酮[4,3-b]吡咯啶
I. Synthesis of Functionalized Benzofurans from para-Quinone Methides via Phospha-1,6-Addition/O-Acylation/Wittig Pathway II. Phosphine-catalyzed Chemoselective Reduction/Elimination/Wittig Reaction Sequence for Synthesis of Functionalized 3-Alkenyl Benzofurans III. Enantioselective Construction of Chromeno[4,3-b]pyrrolidines from Meldrum’s Acid Alkylidenes and Azomethide Ylides via the (3+2) Cycloaddition/Lactonization Pathway
指導教授： 林文偉
Lin, Wenwei
口試委員： 林文偉
Lin, Wenwei
張永俊
Jang, Yeong-Jiunn
陳焜銘
Chen, Kwunmin
姚清發
Yao, Ching-Fa
劉維民
Liu, Wei-Min
口試日期： 2022/07/15
學位類別： 博士
Doctor
系所名稱： 化學系
Department of Chemistry
論文出版年： 2022
畢業學年度： 110
語文別： 中文
論文頁數： 310
中文關鍵詞： 苯并呋喃 、膦試劑 、分子內威悌反應 、對亞甲基苯醌 、3-烯基苯并呋喃 、催化膦 、威悌反應 、亞硝酸脫除 、亞胺葉立德 、米氏酸 、不對稱催化 、𠳭酮[4,3-b]吡咯啶
英文關鍵詞： 1,6-Addition, 2,3-Diarylbenzofuran, Wittig reaction, Catalytic Wittig reaction, Nitrous acid elimination, 3-Alkenylbezofuran, Chromeno[4,3-b]pyrrolidine, Asymmetric catalyst, Azomethide ylide, Meldrum’s acid
研究方法: 實驗設計法 、 行動研究法
DOI URL： http://doi.org/10.6345/NTNU202201092
論文種類： 學術論文
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    • (一)穩定的鄰羥基對亞甲基苯醌化合物通過有機膦、醯氯和鹼處理，在無金屬且溫和條件下，有效合成官能化的苯并呋喃。同時，在催化條件下亦證明此一鍋化法之1,6-膦加成/氧-醯化/威悌反應，具有相似的合成官能化苯并呋喃的功效。

    (二)經由使用催化量的膦試劑進行分子內威悌反應，提供在無金屬條件下建構官能化 3-烯基苯并呋喃的有效方法。該一鍋化反應是通過將有機膦進行麥可加成到氧-醯化之硝基苯乙烯而引發，其中膦是通過用苯基矽烷對氧化膦進行化學選擇性還原而生成，從而產生膦葉立德，通過氧-醯化/亞硝酸消除/威悌反應製備多官能化的 3-烯基苯并呋喃衍生物。

    (三)亞烷基米氏酸與亞胺葉立德經由硫脲片段衍生之金雞納鹼催化下，在短時間內進行 (3+2) 環加成/酯交換反應，在短時間內建構優異產率與鏡像選擇性之𠳭酮[4,3-b]吡咯啶衍生物。此外，我們根據實驗結果的發現，提出了催化劑與亞烷基米氏酸活化的反應模型。

    (一)An efficient synthesis of functionalized benzofurans is achieved under mild and metal free conditions from stable para-quinone methides by treatment with phosphine, acyl chloride, and a base. This one-pot phospha-1,6-addition/O-acylation/Wittig reaction is also demonstrated under catalytic conditions with similar efficacy.

    (二)A highly efficient protocol for the synthesis of functionalized 3-alkenyl benzofurans is demonstrated under metal-free conditions using catalytic amount of phosphine proceeding an intramolecular Wittig reaction. This one-pot reaction was initiated by the phospha-Michael addition of phosphine to O-acylated nitrostyrene, in which phosphine was in-situ generated from the chemoselective reduction of phosphine oxide with PhSiH3, would provide the phosphorus ylide to result in the aforementioned multifunctionalized benzofuran via O-acylation/nitrous acid elimination/Wittig reaction.

    (三)A quinine-derived thiourea-catalyzed enantioselective (3+2) cycloaddition/desymmetrization transesterification reaction of Meldrum’s acid alkylidenes with azomethine ylides is realized in minute-scale. The desired chromeno[4,3-b]pyrrolidines were obtained in moderate to excellent yields with excellent stereoselectivities. Moreover, a plausible dual activation catalytic model via the hydrogen bonding interaction of the moiety of catalyst towards Meldrum’s acid alkylidene was proposed according to the findings in this study.

    序章 1 膦試劑用於建構碳-碳單鍵 1 膦試劑用於建構碳-碳雙鍵 2 膦試劑用於進行官能基轉換 3 膦試劑用於合成雜環 5 第一部分 使用鄰羥基對亞甲基苯醌經由 1,6-膦加成/氧-醯化/威悌反應建構官能化苯并呋喃衍生物 9 1-1 前言 9 1-1-1 對亞甲基苯醌之介紹 9 1-1-2 鄰羥基之 p-QMs 用於合成雜環 10 1-1-3 2,3-二芳基苯并呋喃之生物活性 12 1-1-4 2,3-二芳基苯并呋喃之合成方式 12 1-2 研究動機 13 1-3 研究結果與討論 15 1-3-1反應條件優化－膦試劑與溶劑篩選 15 1-3-2反應條件優化－鹼試劑與其當量數及其他條件的篩選 16 1-3-3醯氯取代基效應探討 18 1-3-4 使用催化量的膦試劑進行反應 20 1-3-5反應機構探討 21 1-4結論 26 1-5 光譜解析 26 1-6 實驗部分 31 1-6-1 分析儀器 31 1-6-2 實驗操作步驟 31 1-6-3 光譜數據 32 參考文獻 49 附件一、NMR光譜數據 52 附件二、X-ray 單晶繞射數據 72 附件三 檢查清單 74 第二部分 膦催化之化學選擇性還原/亞硝酸離去/威悌反應建構 3-烯基苯并呋喃衍生物 75 2-1 前言 75 2-1-1 硝基官能團在合成上的應用 75 2-1-2 硝基烷做為拉電子基團及親核性前驅物的應用 76 2-1-3 硝基烯烴的應用 77 2-1-4 硝基化合物在雙鍵建構的應用 78 2-2 研究動機 80 2-3 研究結果與討論 84 2-3-1 反應條件優化－膦試劑當量及反應溫度篩選 84 2-3-2 反應條件優化－溶劑篩選 85 2-3-3 催化膦系統介紹 88 2-3-4 催化膦系統應用於分子內 Wittig 反應之條件優化 90 2-3-5 鄰-羥基硝基苯乙烯於催化型 Wittig 反應之取代基效應探討 93 2-3-6 克級合成 97 2-3-7 反應機構探討 97 2-4結論 101 2-5 光譜解析 102 2-6 實驗部分 106 2-6-1 分析儀器 106 2-6-2 實驗操作步驟 106 2-6-3 光譜數據 110 參考文獻 143 附件一、NMR 光譜數據 145 附件二、 X-ray 單晶繞射數據 187 附件三 檢查清單 189 第三部分 亞烷基米氏酸與亞胺葉立德經 (3+2) 環加成/內酯化反應合成高鏡像選擇性之𠳭酮[4,3-b]吡咯啶 190 3-1 前言 190 3-1-1 有機催化概述 190 3-1-2 Chromenopyrrolidines的介紹 191 3-1-3 1,3-偶極體介紹 192 3-1-4米氏酸介紹 199 3-1-4-1 米氏酸作為試劑 200 3-1-4-2 亞烷基米氏酸在合成上的應用 201 3-2 研究動機 202 3-3 結果與討論 203 3-3-1 反應條件優化-催化劑篩選 203 3-3-2 反應條件優化-溶劑篩選 205 3-3-3 反應條件優化-濃度與催化劑使用量 206 3-3-4 反應條件優化-起始物當量篩選 207 3-3-5 取代基效應探討 209 3-3-6 克級合成 211 3-3-7 118a 之鏡像異構物之合成 212 3-3-8 反應機構探討 212 3-4 未來展望 213 3-5 結論 214 3-6 光譜解析 215 3-7 實驗部分 221 3-7-1 分析儀器 221 3-7-2 實驗操作步驟 222 3-7-3 光譜數據 226 參考文獻 253 附件一、NMR 光譜資料 255 附件二、X-ray 單晶繞射數據 281 附件三、高效液相層析 (HPLC) 數據 282 附件四、檢查清單 309 附件五、博士班期間完成的論文發表 310

    1. (a) Corey, E. J.; Fuchs, P. L. Tetrahedron Lett., 1972, 13, 3769-3772. (b) Eymery, F.; Iorga, B.; Savignac, P. Synthesis 2000, 2000, 185-213. (c) Fu, X.; Loh, W.-T.; Zhang, Y.; Chen, T.; Ma, T.; Liu, H.; Wang, J.; Tan, C.-H. Angew. Chem. Int. Ed. 2009, 48, 7387-7390. (d) Wonneberger, P.; König, N.; Kraft, F. B.; Sárosi, M. B.; Hey-Hawkins, E. Angew. Chem. Int. Ed. 2019, 58, 3208-3211.
    2. Horner, L.; Jurgeleit, W.; Klupfel, K. Liebigs Ann. Chem. 1955, 591, 108−117.
    3. Rauhut, M. M.; Currier, H. U.S. Patent 3074999, 1963; Chem. Abstr. 1963, 58, 66109.
    4. Morita, K.; Suzuki, Z.; Hirose, H. Bull. Chem. Soc. Jpn. 1968, 41, 2815−2816.
    5. Baylis, A. B.; Hillman, M. E. D. German Patent 2155113, 1972; Chem. Abstr. 1972, 77, 34174.
    6. (a) Wittig, G.; Geissler, G. Liebigs Ann. Chem, 1953, 580, 44-57. (b) Wittig, G.; Schöllkopf, U. Chem. Ber. 1954, 97, 1318-1330. (c) Wittig, G.; Haag, W. Chem. Ber. 1955, 88, 1654-1656.
    7. Horner, L.; Hoffmann, H.; Wippel, H. G. Chem. Ber. 1958, 91, 61-63.
    8. Wadsworth, W. S.; Emmons, W. D. J. Am. Chem. Soc. 1961, 83, 1733-1738.
    9. Staudinger, H.; Meyer, J. Helv. Chim. Acta. 1919, 2, 635-646.
    10. (a) Gololobov, Y. G.; Zhmurova, I. N.; Kasukhin, L. F. Tetrahedron 1981, 37, 437-472. (b) Molina, P., Vilaplana, M. J. Synthesis 1994, 1994, 1197-1218.
    11. Appel, R. Angew. Chem. Int. Ed. 1975, 14, 801-811.
    12. (a) Mitsunobu, O.; Yamada, M. Bull. Chem. Soc. Jpn. 1967, 40, 2380-2382. (b) Mitsunobu, O. Synthesis 1981, 1981, 1-28.
    13. Kao, T.-T.; Syu, S.-E.; Jhang, Y.-W.; Lin, W. Org. Lett. 2010, 12, 3066–3069.
    14. (a) Wang, D.-W.; Syu, S.; Hung, Y.-T.; Chen, P.; Lee, C. J.; Chen, K.-W.; Chen, Y.-J.; Lin, W. Org. Biomol. Chem. 2011, 9, 363-366. (b) Jang, Y.-J.; Syu, S.; Chen, Y.-J.; Yang, M.-C.; Lin, W. Org. Biomol. Chem. 2012, 10, 843-847. (c) Tsai, Y.-L.; Das, U.; Syu, S.; Lee, C.-J.; Lin, W. Eur. J. Org. Chem. 2013, 2013, 4634-4641.
    15. Tsai, Y.-L.; Fan, Y.-S.; Lee, C.-J.; Huang, C.-H.; Das, U.; Lin, W. Chem. Commun. 2013, 49, 10266-10268.
    16. Lee, Y.-T.; Jang, Y.-J.; Syu, S.-e.; Chou, S.-C.; Lee, C.-J.; Lin, W. Chem. Commun. 2012, 48, 8135-8137.
    17. (a) Yang, S.-M.; Wang, C.-Y.; Lin, C.-K.; Karanam, P.; Reddy, G. M.; Tsai, Y.-L.; Lin, W. Angew. Chem. Int. Ed. 2018, 57, 1668-1672. (b) Chen, Y.-R.; Reddy, G. M.; Hong, S.-H.; Wang, Y.-Z.; Yu, J.-K.; Lin, W. Angew. Chem. Int. Ed. 2017, 56, 5106-5110.
    18. Syu, S.-e.; Lee, Y.-T.; Jang, Y.-J.; Lin, W. Org. Lett. 2011, 13, 2970–2973.
    19. Jansen, R.; Gerth, K.; Steinmetz, H.; Reinecke, S.; Kessler, W.; Kirschning, A.; Müller, R. Chem. Eur. J. 2011, 17, 7739-7744.
    20. Takao, K.-i.; Sasaki, T.; Kozaki, T.; Yanagisawa, Y.; Tadano, K.-i.; Kawashima, A.; Shinonaga, H. Org. Lett. 2001, 3, 4291–4294.
    21. Singh, G.; Pandey, R.; Pankhade, Y. A.; Fatma, S.; Anand, R. V. Chem. Rec. 2021, 21, 4150-4173.
    22. Gao, S.; Xu, X.; Yuan, Z.; Zhou, H.; Yao, H.; Lin, A. Eur. J. Org. Chem. 2016, 2016, 3006-3012. (b) Hao, Y.-J.; Hu, X.-S.; Yu, J.-S.; Zhou, F.; Zhou, Y.; Zhou, J. Tetrahedron 2018, 74, 7395-7398. (c) He, F.-S.; Jin, J.-H.; Yang, Z.-T.; Yu, X.; Fossey, J. S.; Deng, W.-P. ACS Catal. 2016, 6, 652-656.
    23. Chu, W.-D.; Zhang, L.-F.; Bao, X.; Zhao, X.-H.; Zeng, C.; Du, J.-Y.; Zhang, G.-B.; Wang, F.-X.; Ma, X.-Y.; Fan, C.-A. Angew. Chem. Int. Ed. 2013, 52, 9229-9233. (b) Ge, L.; Lu, X.; Cheng, C.; Chen, J.; Cao, W.; Wu, X.; Zhao, G. J. Org. Chem. 2016, 81, 9315–9325.
    24. Deng, Y.-H.; Zhang, X.-Z.; Yu, K.-Y.; Yan, X.; Du, J.-Y.; Huang, H.; Fan, C.-A. Chem. Commun. 2016, 52, 4183-4186. (b) Zhao, K.; Zhi, Y.; Wang, A.; Enders, D. ACS Catal. 2016, 6, 657–660.
    25. Reddy, V. R.; Maripally, N.; Mutyala, R.; Nanubolu, J. B.;Chandra, R. Tetrahedron Lett. 2018, 59, 2631-2635.
    26. Lou, Y.; Cao, P.; Jia, T.; Zhang, Y.; Wang, M.; Liao, J. Angew. Chem. Int. Ed. 2015, 54, 12134-12138. (b) Molleti, N.; Kang, J. Y. Org. Lett. 2017, 19, 958–961. (c) López, A.; Parra, A.; Jarava-Barrera, C.; Tortosa, M. Chem. Commun. 2015, 51, 17684-17687. (d) Dong, N.; Zhang, Z.-P.; Xue, X.-S.; Li, X.; Cheng, J.-P. Angew. Chem. Int. Ed. 2016, 55, 1460-1464.
    27. Zhao, K.; Zhi, Y.; Shu, T.; Valkonen, A.; Rissanen, K.; Enders, D. Angew. Chem. Int. Ed. 2016, 128, 12283-12287.
    28. Zhang, L.; Zhou, X.; Li, P.; Liu, Z.; Liu, Y.; Sun, Y.; Li, W. RSC Adv. 2017, 7, 39216-39220. (b) Cao, Z.; Zhou, G.-X.; Ma, C.; Jiang, K.; Mei, G.-J. Synthesis 2018, 50, 1307-1314. (c) Zhang, L.; Liu, Y.; Liu, K.; Liu, Z.; He, N.; Li, W. Org. Biomol. Chem. 2017, 15, 8743-8747. (d) Mei, G.-J.; Xu, S.-L.; Zheng, W.-Q.; Bian, C.-Y.; Shi, F. J. Org. Chem. 2018, 83, 1414–1421. (e) Jiang, X.-L.; Wu, S.-F.; Wang, J.-R.; Mei, G.-J.; Shi, F. Adv. Synth. Catal. 2018, 360, 4225–4235. (f) Huang, H.-M.; Wu, X.-Y.; Leng, B.-R.; Zhu, Y.-L.; Meng, X.-C.; Hong, Y.; Jiang, B.; Wang, D.-C. Org. Chem. Front. 2020, 7, 414–419. (g) Zhang, Z.-P.; Xie, K.-X.; Yang, C.; Li, M.; Li, X. J. Org. Chem. 2018, 83, 364–373.
    29. Liu, Q.; Li, S.; Chen, X.-Y.; Rissanen, K.; Enders, D. Org. Lett. 2018, 20, 3622-3626. (b) Li, W.; Yuan, H.; Liu, Z.; Zhang, Z.; Cheng, Y.; Li, P. Adv. Synth. Catal. 2018, 360, 2460-2464. (c) Zhou, J.; Liang, G.; Hu, X.; Zhou, L.; Zhou, H. Tetrahedron 2018, 74, 1492-1496.
    30. Liu, L.; Yuan, Z.; Pan, R.; Zeng, Y.; Lin, A.; Yao, H.; Huang, Y. Org. Chem. Front. 2018, 5, 623–628.
    31. Chen, X.-M.; Xie, K.-X.; Yue, D.-F.; Zhang, X.-M.; Xu, X.-Y.; Yuan, W.-C. Tetrahedron 2018, 74, 600–605.
    32. Zhi, Y.; Zhao, K.; von Essen, C.; Rissanen, K.; Enders, D. Org. Chem. Front. 2018, 5, 1348–1351.
    33. Singh, G.; Goswami, P.; Sharma, S.; Anand, R. V. J. Org. Chem. 2018, 83, 10546–10554.
    34. Lee, C.-J.; Chang, T.-H.; Yu, J.-K.; Reddy, G. M.; Hsiao, M.-Y.; Lin, W. Org. Lett. 2016, 18, 3758–3761.
    35. Chen, K.-W.; Syu, S.-e.; Jang, Y.-J.; Lin, W. Org. Biomol. Chem. 2011, 9, 2098-2106.

    1. Rode, C. V.; Gupte, S. P.; Chaudhari, R. V.; Pirozhkov, C. D.; Lapidus, A. L. J. Mol. Catal. 1994, 91, 195-206.
    2. Yoshihisa, W.; Yasushi, T.; Ryo, T. Bull. Chem. Soc. Jpn. 1984, 57, 3011-3012.
    3. Hardy, W. B.; Bennett, R. P. Tetrahedron Lett. 1967, 8, 961-962.
    4. Oh, J. S.; Lee, S. M.; Yeo, J. K.; Lee, C. W.; Lee, J. S. Ind. Eng. Chem. Res. 1991, 30, 1456-1461.
    5. Ono, N.; Miyake, H.; Tamura, R.; Kaji, A. Tetrahedron Lett. 1981, 22, 1705-1708.
    6. Osby, J. O.; Ganem, B. Tetrahedron Lett. 1985, 26, 6413-6416.
    7. Ballini, R.; Bosica, G. Tetrahedron 1995, 51, 4213-4222.
    8. Ballini, R.; Petrini, M. Adv. Synth. Catal. 2015, 357, 2371-2402.
    9. Dong, L.; Chen, F.-E. RSC Adv. 2020, 10, 2313-2326.
    10. Alvarez-Casao, Y.; Marques-Lopez, E.; Herrera, R. P. Symmetry 2011, 3, 220-245. (b) Milner, S. E.; Moody, T. S.; Maguire, A. R. Eur. J. Org. Chem. 2012, 2012, 3059-3067.
    11. Berner, Otto M.; Tedeschi, L.; Enders, D. Eur. J. Org. Chem. 2002, 2002, 1877-1894. (b) Roca-Lopez, D.; Sadaba, D.; Delso, I.; Herrera, R. P.; Tejero, T.; Merino, P. Tetrahedron: Asymmetry 2010, 21, 2561-2601. (c) Halimehjani, A. Z.; Karimi, N.; Saidi, M. R. Synth. Commun. 2013, 43, 744-748.
    12. Noble, A.; Anderson, J. C. Chem. Rev. 2013, 113, 2887-2939.
    13. Satham, L.; Sankara, C. S.; Namboothiri, I. N. N. Eur. J. Org. Chem. 2020, 2020, 6903-6908.
    14. Ganesh, M.; Namboothiri, I. N. N. Tetrahedron 2007, 63, 11973-11983. (b) Greger, J. G.; Yoon-Miller, S. J. P.; Bechtold, N. R.; Flewelling, S. A.; MacDonald, J. P.; Downey, C. R.; Cohen, E. A.; Pelkey, E. T. J. Org. Chem. 2011, 76, 8203-8214.
    15. Halimehjani, A. Z.; Namboothiri, I. N. N.; Hooshmand, S. E. RSC Adv. 2014, 4, 48022-48084.
    16. Awasthi, C.; Yadav, L. D. S. Synlett 2010, 2010, 1783-1788.
    17. Kuroda, Y.; Imaizumi, K.; Yamada, K.-i.; Yamaoka, Y.; Takasu, K. Tetrahedron Lett. 2013, 54, 4073-4075.
    18. Huang, C.-Y.; Kuo, C.-W.; Kavala, V.; Yao, C.-F. Eur. J. Org. Chem. 2016, 2016, 2720-2734.
    19. Ballini, R.; Palmieri, A. Adv. Synth. Catal. 2019, 361, 5070-5097.
    20. Ballini, R.; Fiorini, D.; Palmieri, A. Tetrahedron Lett. 2005, 46, 1245-1246.
    21. Nair, D. K.; Mobin, S. M.; Namboothiri, I. N. N. Org. Lett. 2012, 14, 4580-4583.
    22. Sakiyama, N.; Noguchi, K.; Tanaka, K. Angew. Chem. Int. Ed. 2012, 51, 5976-5980.
    23. Ohno, S.; Qiu, J.; Miyazaki, R.; Aoyama, H.; Murai, K.; Hasegawa, J.-y.; Arisawa, M. Org. Lett. 2019, 21, 8400–8403.
    24. Iqbal, N.; Iqbal, N.; Maiti, D.; Cho, E. J. Angew. Chem. Int. Ed. 2019, 131, 15955-15959.
    25. Ali, M. U.; Fitzpatrick-Lewis, D.; Kenny, M.; Raina, P.; Atkins, D. L.; Soar, J.; Nolan, J.; Ristagno, G.; Sherifali, D. Resuscitation 2018, 132, 63-72.
    26. Liou, Y.-C.; Karanam, P.; Jang, Y.-J.; Lin, W. Org. Lett. 2019, 21, 8008–8012 (b) Yang, S.-M.; Wang, C.-Y.; Lin, C.-K.; Karanam, P.; Reddy, G. M.; Tsai, Y.-L.; Lin, W. Angew. Chem. Int. Ed. 2018, 57, 1668-1672. (c) Fan, Y.-S.; Das, U.; Hsiao, M.-Y.; Liu, M.-H.; Lin, W. J. Org. Chem. 2014, 79, 11567–11582. (d) Lee, Y.-T.; Jang, Y.-J.; Syu, S.-e.; Chou, S.-C.; Lee, C.-J.; Lin. W. Chem. Commun. 2012, 48, 8135-8137.
    27. Kolodiazhnyi, O. I.; Kolodiazhna, O. O. Syn. Commun. 2012, 42, 1637-1649.
    28. Li, S.-N.; Xu, L.-T.; Chen, Y.; Li, J.-L.; He, L. Lett. Org. Chem. 2011, 8, 416-422.
    29. Freeman, A. W.; Urvoy, M.; Criswell, M. E. J. Org. Chem. 2005, 70, 5014–5019.
    30. Creencia, E. C.; Kosaka, M.; Muramatsu, T.; Kobayashi, M.; Iizuka, T.; Horaguchi, T. J. Heterocyclic Chem., 2009, 46, 1309-1317. (b) Balaji, G.; Shim, W. L.; Parameswaran, M.; Valiyaveettil, S. Org. Lett. 2009, 11, 4450–4453.
    31. Carter, M. E.; Nash Jr., J. L.; Drueke Jr., J. W.; Schwietert, J. W.; Butler, G. B. J. Polym. Sci. Polym. Chem. Ed. 1978, 16, 937-959.
    32. Campbell, T. W.; Monagle, J. J. J. Am. Chem. Soc. 1962, 84, 1493.
    33. Marsden, S. P.; McGonagle, A. E.; McKeever-Abbas, B. Org. Lett. 2008, 10, 2589–2591.
    34. O'Brien, C. J.; Tellez, J. L.; Nixon, Z. S.; Kang, L. J.; Carter, A. L.; Kunkel, S. R.; Przeworski, K. C.; Chass, G. A. Angew. Chem. Int. Ed. 2009, 48, 6836-6839.
    35. Lee, C.-J.; Chang, T.-H.; Yu, J.-K.; Reddy, G. M.; Hsiao, M.-Y.; Lin, W. Org. Lett. 2016, 18, 3758-3761.
    36. Gao, Y.; Yang, S.; Huo, Y.; Hu, X.-Q. Adv. Synth. Catal. 2020, 362, 3971-3986.
    37. Kodukulla, R. P. K.; Trivedi, G. K.; Vora, J. D.; Mathur, H. H. Syn. Comm. 1994, 24, 819-832.

    1. Vashistha, V. K.; Sethi, S.; Tyagi, I.; Das, D. K. Asian Bio. 2022, 16, 55-69. (b) Boussouar, I.; Chen, Q.; Chen, X.; Zhang, Y.; Zhang, F.; Tian, D.; White, H. S.; Li, H. Anal. Chem. 2017, 89, 1110–1116. (c) Saha, D.; Kharbanda, A.; Yan, W.; Lakkaniga, N. R.; Frett, B.; Li, H.-Y. J. Med. Chem. 2020, 63, 441–469.
    2. Hussain, K.; Patel, P.; Roberts, N. Clin Exp Dermatol, 2022, 47: 667-674. (b) Gao, S.; Wang, S.; Fan, R.; Hu, J. Bio. & Pharm. 2020, 127, 110114-110119.
    3. Yutthalekha, T.; Wattanakit, C.; Lapeyre, V.; Nokbin, S.; Warakulwit, C.; Limtrakul, J.; Kuhn, A. Nat. Commun. 2016, 7, 12678-12685.
    4. Żądło-Dobrowolska, A.; Koszelewski, D.; Paprocki, D.; Madej, A.; Wilk, M.; Ostaszewski, R. ChemCatChem 2017, 9, 3047-3057.
    5. Dondoni, A.; Massi, A. Angew. Chem. Int. Ed. 2008, 47, 4638-4660.
    6. Chekan, J. R.; McKinnie, S. M. K.; Moore, M. L.; Poplawski, S. G.; Michael, T. P.; Moore, B. S. Angew. Chem. Int. Ed. 2019, 58, 8454-8457. (b) Traber, M. G., Vitamin E. Adv. Nut. 2021, 12, 1047-1048.
    7. Haight, A. R.; Bailey, A. E.; Baker, W. S.; Cain, M. H.; Copp, R. R.; DeMattei, J. A.; Ford, K. L.; Henry, R. F.; Hsu, M. C.; Keyes, R. F.; King, S. A.; McLaughlin, M. A.; Melcher, L. M.; Nadler, W. R.; Oliver, P. A.; Parekh, S. I.; Patel, H. H.; Seif, L. S.; Staeger, M. A.; Wayne, G. S.; Wittenberger, S. J.; Zhang, W. Org. Proc. Res. Dev. 2004, 8, 897–902.
    8. Dubuffet, T.; Newman-Tancredi, A.; Cussac, D.; Audinot, V.; Loutz, A.; Millan, M. J.; Lavielle, G. Bio. Med. Chem. Lett. 1999, 9, 2059-2064.
    9. Cao, J.; Liu, J.-Y.; Zhang, Y.-M.; Wang, Z.-Y.; Xu, P.-F. Org. Chem. Front. 2019, 6, 674-678.
    10. Painter, T. O.; Kaszas, K.; Gross, J.; Douglas, J. T.; Day, V. W.; Iadarola, M. J.; Santini, C. Bio. Med. Chem. Lett. 2014, 24, 963-968.
    11. Esteban, F.; Cieślik, W.; Arpa, E. M.; Guerrero-Corella, A.; Díaz-Tendero, S.; Perles, J.; Fernández-Salas, J. A.; Fraile, A.; Alemán, J. ACS Catal. 2018, 8, 3, 1884–1890. (b) Cao, J.; Fang, R.; Liu, J.-Y.; Lu, H.; Luo, Y.-C.; Xu, P.-F. Chem. Eur. J. 2018, 24, 18863-18867.
    12. Breugst, M.; Reissig, H.-U. Angew. Chem. Int. Ed. 2020, 59, 12293-12307.
    13. Yang, Z.-X.; Wei, Y.-Q.; Yang, C.; Li, Y.-F.; Ding, C.-H.; Xu, B. Asian J. Org. Chem. 2022, 11, e202100683. (b) Acharya, A.; Montes, K.; Jeffrey, C. S. Org. Lett. 2016, 18, 6082–6085.
    14. Obydennov, D. L.; Steben’kov, V. D.; Obydennov, K. L.; Usachev, S. A.; Moshkin, V. S.; Sosnovskikh, V. Y. Synthesis 2021, 53, 2621-2631.
    15. Tu, L.; Li, Z.; Feng, T.; Yu, S.; Huang, R.; Li, J.; Wang, W.; Zheng, Y.; Liu, J. J. Org. Chem. 2019, 84, 11161–11169.
    16. Domingo, L. R.; Ríos-Gutiérrez, M.; Pérez, P. J. Org. Chem. 2018, 83, 10959–10973.
    17. Przydacz, A.; Bojanowski, J.; Albrecht, A.; Albrecht, Ł. Org. Biomol. Chem. 2021, 19, 3075-3086.
    18. Chang, G.-H.; Wang, C.-Y.; Madhusudhan Reddy, G.; Tsai, Y.-L.; Lin, W. J. Org. Chem. 2016, 810, 10071–10080.
    19. Yang, S.-M.; Reddy, G. M.; Wang, T.-P.; Yeh, Y.-S.; Wang, M.; Lin, W. Chem. Commun. 2017, 53, 7649-7652.
    20. Yu, J.-K.; Chien, H.-W.; Lin, Y.-J.; Karanam, P.; Chen, Y.-H.; Lin, W. Chem. Commun. 2018, 54, 9921-9924.
    21. Li, T.; Wang, J.; Xu, J.; Jin, J.; Chi, Y. R.; Jin, Z. Org. Lett. 2020, 22, 326–330.
    22. Tian, L.; Xu, G.-Q.; Li, Y.-H.; Liang, Y.-M.; Xu, P.-F. Chem. Commun. 2014, 50, 2428-2430.
    23. Kowalczyk, D.; Albrecht, Ł. J. Org. Chem. 2016, 81, 6800–6807.
    24. Meldrum, A. N. J. Chem. Soc. Trans. 1908, 93, 598-601.
    25. Davidson, D.; Bernhard, S. A., J. Am. Chem. Soc, 1948, 70, 3426–3428.
    26. Pfluger, C. E.; Boyle, P. D. J. Chem. Soc., Perkin Trans. 2, 1985, 1547-1549.
    27. Brosge, F.; Singh, P.; Almqvist, F.; Bolm, C. Org. Biomol. Chem. 2021, 19, 5014-5027.
    28. List, B.; Castello, C. Synlett 2001, 2001, 1687-1689.
    29. Shi, J.; Liu, Y.; Wang, M.; Lin, L.; Liu, X.; Feng, X. Tetrahedron 2011, 67, 1781-1787.
    30. Berini, C.; Sebban, M.; Oulyadi, H.; Sanselme, M.; Levacher, V.; Brière, J.-F. Org. Lett. 2015, 17, 5408–5411.
    31. Belot, V.; Farran, D.; Jean, M.; Albalat, M.; Vanthuyne, N.; Roussel, C. J. Org. Chem. 2017, 82, 10188-10200.
    32. Dumas, A. M.; Seed, A.; Zorzitto, A. K.; Fillion, E. Tetrahedron Lett. 2007, 48, 7072-7074.

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