Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (7): 2407-2424.DOI: 10.6023/cjoc202210035 Previous Articles Next Articles
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收稿日期:
2022-10-28
修回日期:
2023-01-16
发布日期:
2023-02-06
通讯作者:
周林
基金资助:
Lin Zhou(), Hong Yang, Chuan Yang, Zhigang Zhao, Qinghan Li
Received:
2022-10-28
Revised:
2023-01-16
Published:
2023-02-06
Contact:
Lin Zhou
Supported by:
Share
Lin Zhou, Hong Yang, Chuan Yang, Zhigang Zhao, Qinghan Li. Advances on the α- and β-Reactions of Deconjugated Butenolides[J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2407-2424.
[1] |
For selected reviews and examples, see: (a) Kitson, R.R.A.; Millemaggi, A.; Taylor, R., J. K. Angew. Chem., Int. Ed. 2009, 48, 9426.
pmid: 16468720 |
(b) Lone, S. H.; Bhat, K. A.; Khuroo, M. A. Chem.-Biol. Interact. 2015, 240, 180.
doi: 10.1016/j.cbi.2015.08.015 pmid: 16468720 |
|
(c) Yu, X.; Che, Z.; Xu, H. Chem.-Eur. J. 2017, 23, 4467.
doi: 10.1002/chem.201602472 pmid: 16468720 |
|
(d) Curti, C.; Battistini, L.; Sartori, A.; Zanardi, F. Chem. Rev. 2020, 120, 2448.
doi: 10.1021/acs.chemrev.9b00481 pmid: 16468720 |
|
(e) Choudhury, A. R.; Mukherjee, S. Chem. Soc. Rev. 2020, 49, 6755.
doi: 10.1039/c9cs00346k pmid: 16468720 |
|
(f) Boeckman, R. K.; Pero, J. E.; Boehmler, D. J. J. Am. Chem. Soc. 2006, 128, 11032.
pmid: 16468720 |
|
(g) Robichaud, J.; Tremblay, F. Org. Lett. 2006, 8, 597.
pmid: 16468720 |
|
(h) Zhang, X.; Yin, Y.; Zhou, Y.; Zhu, T.; Wang, M.; Gao, H. Chin. J. Chem. 2022, 40, 617.
doi: 10.1002/cjoc.v40.5 pmid: 16468720 |
|
(i) You, J.-Q.; Liu, Y.-N.; Zhou, J.-S.; Sun, X.-Y.; Lei, C.; Mu, Q.; Li, J.-Y.; Hou, A.-J. Chin. J. Chem. 2022, 40, 2882.
doi: 10.1002/cjoc.v40.24 pmid: 16468720 |
|
(j) Zhang, H.; Nan, F. Chin. J. Chem. 2013, 31, 84.
doi: 10.1002/cjoc.201200695 pmid: 16468720 |
|
(k) Tang, B.; Guan, A.; Zhao, Y.; Jiang, J.; Wang, M.; Zhou, L. Chin. J. Chem. 2017, 35, 1133.
doi: 10.1002/cjoc.v35.7 pmid: 16468720 |
|
(l) Wang, Y.; Chen, B.; He, X.; Gui, J. Chin. J. Chem. 2020, 38, 1339.
doi: 10.1002/cjoc.v38.11 pmid: 16468720 |
|
[2] |
(a) Ma, S.-M.; Shi, Z.-J. Chin. J. Chem. 2001, 19, 1280.
doi: 10.1002/cjoc.20010191220 |
(b) Wang, J. P.; Chang, X. H.; Tian, X. Z.; Chen, Q. H. Acta Chim. Sinica 2003, 61, 411 (in Chinese).
|
|
(王建平, 常新红, 田欣哲, 陈庆华, 化学学报, 2003, 61, 411.)
|
|
(c) Zhao, Y.; Jiang, S.; Guo, Y.-W.; Yao, Z.-J. Chin. J. Chem. 2005, 23, 173.
doi: 10.1002/(ISSN)1614-7065 |
|
(d) Zhao, Y.; Tang, B.; Liu, X.; Li, W. Z.; Huang, M. Y.; Wang, M. A. Chin. J. Org. Chem. 2017, 37, 975 (in Chinese).
doi: 10.6023/cjoc201611013 |
|
(赵宇, 汤博, 刘鑫磊, 李婉祯, 黄铭一, 王明安, 有机化学, 2017, 37, 975.)
doi: 10.6023/cjoc201611013 |
|
(e) Li, X.; Zhu, K.; Han, Q.; Lu, X. X.; Li, M. J.; Ling, Y.; Duan, H. X. Chin. J. Org. Chem. 2022, 42, 202 (in Chinese).
|
|
(李想, 朱凯, 韩清, 路星星, 李明君, 凌云, 段红霞, 有机化学, 2022, 42, 202.)
|
|
(f) Zhang, Q.; Li, Y. H.; Xu, L. C.; Ma, H. Y.; Li, X. D.; Wang, M. A. Chin. J. Org. Chem. 2022, 42, 2438 (in Chinese).
doi: 10.6023/cjoc202203033 |
|
(张倩, 李益豪, 许磊川, 马好运, 李向东, 王明安, 有机化学, 2022, 42, 2438.)
doi: 10.6023/cjoc202203033 |
|
[3] |
(a) Das, U.; Chen, Y.-R.; Tsai, Y.-L.; Lin, W. Chem.-Eur. J. 2013, 19, 7713.
doi: 10.1002/chem.v19.24 |
(b) Rout, S.; Das, A.; Singh, V. K. Chem. Commun. 2017, 53, 5143.
doi: 10.1039/C7CC01763D |
|
[4] |
(a) Adekenov, S. M.; Mukhametzhanov, M. N.; Kagarlitskii, A. D.; Kupriyanov, A. N. Khim. Prir. Soedin. 1982, 655.
|
(b) Zhangabylov, N. S.; Dederer, L. Y.; Gorbacheva, L. B.; Vasilêva, S. V.; Terekhov, A. S.; Adekenov, S. M. Pharm. Chem. J. 2004, 38, 651.
doi: 10.1007/s11094-005-0052-9 |
|
[5] |
Aubert, S.; Katsina, T.; Arseniyadis, S. Org. Lett. 2019, 21, 2231.
doi: 10.1021/acs.orglett.9b00521 |
[6] |
For selected reviews, see: (a) Jusseau, X.; Chabaud, L.; Guillou, C. Tetrahedron 2014, 70, 2595.
doi: 10.1016/j.tet.2014.01.057 |
(b) Roselló, M. S.; del Pozoa, C.; Fustero, S. Synthesis 2016, 48, 2553.
doi: 10.1055/s-0035-1561650 |
|
(c) Mao, B.; Fañanas-Mastral, M.; Feringa, B. L. Chem. Rev. 2017, 117, 10502.
doi: 10.1021/acs.chemrev.7b00151 |
|
(d) Yin, Y.; Jiang, Z. ChemCatChem 2017, 9, 4306.
doi: 10.1002/cctc.v9.23 |
|
(e) Li, H.; Yin, L. Tetrahedron Lett. 2018, 59, 4121.
doi: 10.1016/j.tetlet.2018.10.012 |
|
[7] |
For selected examples on activated silyloxyfurans, see: (a) Redero, E.; Sandoval, C.; Bermejo, F. Tetrahedron 2001, 57, 9597.
pmid: 20583835 |
(b) Singh, R. P.; Foxman, B. M.; Deng, L. J. Am. Chem. Soc. 2010, 132, 9558.
doi: 10.1021/ja103331t pmid: 20583835 |
|
(c) Meshram, H. M.; Ramesh, P.; Reddy, B. C.; Sridhar, B.; Yadav, J. S. Tetrahedron 2011, 67, 3150.
doi: 10.1016/j.tet.2011.02.033 pmid: 20583835 |
|
(d) Mao, B.; Ji, Y.; Fananas-Mastral, M.; Caroli, G.; Meetsma, A.; Feringa, B. L. Angew. Chem., Int. Ed. 2012, 51, 3168.
doi: 10.1002/anie.v51.13 pmid: 20583835 |
|
(e) Chen, W.; Hartwig, J. F. J. Am. Chem. Soc. 2012, 134, 15249.
doi: 10.1021/ja306850b pmid: 20583835 |
|
(f) Woyciechowska, M.; Forcher, G.; Buda, S.; Mlynarski, J. Chem. Commun. 2012, 48, 11029.
doi: 10.1039/c2cc36656h pmid: 20583835 |
|
(g) Kong, S.; Fan, W.; Lyu, H.; Zhan, J.; Miao, X.; Miao, Z. Synth. Commun. 2014, 44, 936.
doi: 10.1080/00397911.2013.837926 pmid: 20583835 |
|
(h) Wang, Y.; Xing, F.; Xue, M.; Du, G.-F.; Guo, X.-H.; Huang, K.-W.; Dai, B. Synthesis 2016, 48, 79.
doi: 10.1055/s-00000084 pmid: 20583835 |
|
(i) Adamkiewicz, A.; Węglarz, I.; Butkiewicz, A.; Woyciechowska, M.; Mlynarski, J. Adv. Synth. Catal. 2020, 362, 667.
doi: 10.1002/adsc.v362.3 pmid: 20583835 |
|
[8] |
(a) Zhang, Y.; Yu, C.; Ji, Y.; Wang, W. Chem.-Asian J. 2010, 5, 1303.
|
(b) Huang, H.; Yu, F.; Jin, Z.; Li, W.; Wu, W.; Liang, X.; Ye, J. Chem. Commun. 2010, 46, 5957.
doi: 10.1039/c0cc01054e |
|
(c) Luo, J.; Wang, H.; Han, X.; Xu, L.-W.; Kwiatkowski, J.; Huang, K.-W.; Lu, Y. Angew. Chem., Int. Ed. 2011, 50, 1861.
doi: 10.1002/anie.v50.8 |
|
(d) Yin, L.; Takada, H.; Lin, S.; Kumagai, N.; Shibasaki, M. Angew. Chem., Int. Ed. 2014, 53, 5327.
doi: 10.1002/anie.v53.21 |
|
[9] |
(a) Cui, H. L.; Huang, J. R.; Lei, J.; Wang, Z. F.; Chen, S.; Wu, L.; Chen, Y. C. Org. Lett. 2010, 12, 720.
doi: 10.1021/ol100014m |
(b) Wu, Y.; Singh, R. P.; Deng, L. J. Am. Chem. Soc. 2011, 133, 12458.
doi: 10.1021/ja205674x |
|
(c) Griswold, J. A.; Johnson, J. S. ACS Catal. 2019, 9, 11614.
doi: 10.1021/acscatal.9b04405 |
|
(d) Yu, C.; Ji, P.; Zhang, Y.; Meng, X.; Wang, W. Org. Lett. 2021, 23, 7656.
doi: 10.1021/acs.orglett.1c02916 |
|
(e) Dai, Z.-Y.; Wang, P.-S.; Gong, L.-Z. Chem. Commun. 2021, 57, 6748.
doi: 10.1039/D1CC02295D |
|
[10] |
(a) Helberger, V. J. H.; Ulubey, S.; Civelekoglu, H. Justus Liebigs Ann. Chem. 1949, 561, 215.
doi: 10.1002/(ISSN)1099-0690 |
(b) Karwa, S.; Gajiwala, V. M.; Heltzel, J.; Patil, S. K. R.; Lund, C. R. F. Catal. Today 2016, 263, 16.
doi: 10.1016/j.cattod.2015.06.020 |
|
[11] |
Pelter, A.; Rowlands, M. Tetrahedron Lett. 1987, 28, 1203.
|
[12] |
Marshall, J. A.; Wolf, M. A.; Wallace, E. M. J. Org. Chem. 1997, 62, 367.
pmid: 11671411 |
[13] |
(a) Osman, N. A.; Mahmoud, A. H.; Allara, M.; Niess, R.; Abouzid, K. A.; Marzo, V. D.; Abadi, A. H. Bioorg. Med. Chem. 2010, 18, 8463.
doi: 10.1016/j.bmc.2010.10.050 pmid: 19606900 |
(b) Muratore, M. E.; Holloway, C. A.; Pilling, A. W.; Storer, R. I.; Trevitt, G.; Dixon, D. J. J. Am. Chem. Soc. 2009, 131, 10796.
doi: 10.1021/ja9024885 pmid: 19606900 |
|
[14] |
Lima, C. G. S.; Monteiro, J. L.; Lima, T. Paixão, M. W.; Corrêa, A. G. ChemSusChem. 2018, 11, 25.
doi: 10.1002/cssc.v11.1 |
[15] |
For selected recent reports on the γ-addition of deconjugated butenolides, see: (a) Quintard, A.; Lefranc, A.; Alexakis, A. Org. Lett. 2011, 13, 1540.
doi: 10.1021/ol200235j pmid: 22952199 |
(b) Zhou, L.; Lin, L.-L.; Ji, J.; Xie, M.-S.; Liu, X.-H.; Feng, X.-M. Org. Lett. 2011, 13, 3056.
doi: 10.1021/ol200939t pmid: 22952199 |
|
(c) Zhang, W.; Tan, D.; Lee, R.; Tong, G.; Chen, W.; Qi, B.; Huang, K.-W.; Tan, C.-H.; Jiang, Z. Angew. Chem., Int. Ed. 2012, 51, 10069.
doi: 10.1002/anie.201205872 pmid: 22952199 |
|
(d) Manna, M. S.; Kumar, V.; Mukherjee, S. Chem. Commun. 2012, 48, 5193.
doi: 10.1039/C2CC31700A pmid: 22952199 |
|
(e) Manna, M. S.; Mukherjee, S. Chem.-Eur. J. 2012, 18, 15277.
doi: 10.1002/chem.v18.48 pmid: 22952199 |
|
(f) Ji, J.; Lin, L.-L.; Zhou, L.; Zhang, Y.-H.; Liu, Y.-B.; Liu, X.-H.; Feng X.-M. Adv. Synth. Catal. 2013, 355, 2764.
pmid: 22952199 |
|
(g) Yang, D.; Wang, L.; Zhao, D.; Han, F.; Zhang, B.; Wang, R. Chem.-Eur. J. 2013, 19, 4691.
doi: 10.1002/chem.201204466 pmid: 22952199 |
|
[16] |
For selected reports on the γ-addition of deconjugated butenolides, see: (a) Guo, Y.-L.; Jia, L.-N.; Peng, L.; Qi, L.-W.; Zhou, J.; Tian, F.; Xu, X.-Y.; Wang, L. -X. RSC Adv. 2013, 3, 16973.
doi: 10.1039/c3ra43344g |
(b) Kumar, V.; Ray, B.; Rathi, P.; Mukherjee, S. Synthesis 2013, 45, 1641.
doi: 10.1055/s-00000084 |
|
(c) Manna, M. S.; Mukherjee, S. Chem. Sci. 2014, 5, 1627.
doi: 10.1039/C3SC53102C |
|
(d) Li, X.; Lu, M.; Dong, Y.; Wu, W.; Qian, Q.; Ye, J.; Dixon, D. J. Nat. Commun. 2014, 4, 4479.
|
|
(e) Wang, Z.-H.; Wu, Z.-J.; Huang, X.-Q.; Yue, D.-F.; You, Y.; Xu, X.-Y.; Zhang, X.-M.; Yuan, W.-C. Chem. Commun. 2015, 51, 15835.
doi: 10.1039/C5CC06383C |
|
(f) Guo, H.; Xing, F.; Du, G.-F.; Huang, K.-W.; Dai, B.; He, L. J. Org. Chem. 2015, 80, 12606.
doi: 10.1021/acs.joc.5b01845 |
|
[17] |
For selected reports on the γ-addition of deconjugated butenolides, see: (a) Sekikawa, T.; Kitaguchi, T.; Kitaura, H.; Minami, T.; Hatanaka, Y. Org. Lett. 2015, 17, 3026.
doi: 10.1021/acs.orglett.5b01224 pmid: 26646367 |
(b) Lagoutte, R.; Besnard, C.; Alexakis, A. Eur. J. Org. Chem. 2016, 4372.
pmid: 26646367 |
|
(c) Simlandy, A. K.; Mukherjee, S. Org. Biomol. Chem. 2016, 14, 5659.
doi: 10.1039/c5ob02362a pmid: 26646367 |
|
(d) Tang, Q.; Lin, L.-L.; Ji, J.; Hu, H.-P.; Liu, X.-H.; Feng, X.-M. Chem.-Eur. J. 2017, 23, 16447.
doi: 10.1002/chem.v23.65 pmid: 26646367 |
|
(e) Ji, J.; Lin, L.-L.; Tang, Q.; Kang, T.-F.; Liu, X.-H.; Feng, X.-M. ACS Catal. 2017, 7, 3763.
doi: 10.1021/acscatal.7b00590 pmid: 26646367 |
|
(f) Trost, B. M.; Gnanamani, E.; Tracy, J. S.; Kalnmals, C. J. Am. Chem. Soc. 2017, 139, 18198.
doi: 10.1021/jacs.7b11361 pmid: 26646367 |
|
(g) Rout, S.; Joshi, H.; Singh, V. K. Org. Lett. 2018, 20, 2199.
doi: 10.1021/acs.orglett.8b00493 pmid: 26646367 |
|
[18] |
For selected reports on the γ-addition of deconjugated butenolides, see: (a) Sakai, T.; Hirashima, S.; Matsushima, Y.; Nakano, T.; Ishii, D.; Yamashita, Y.; Nakashima, K.; Koseki, Y.; Miura, T. Org. Lett. 2019, 21, 2606.
doi: 10.1021/acs.orglett.9b00574 |
[19] |
Jefford, C. W.; Jaggi, D.; Boukouvalas, J. J. Chem. Soc., Chem. Commun. 1988, 1595.
|
[20] |
Egorova, A. Y.; Timofeeva, Z. Y. Russ. J. Gen. Chem. 2003, 73, 655.
doi: 10.1023/A:1025625511411 |
[21] |
Griswold, J. A.; Horwitz, M. A.; Leiva, L. V.; Johnson, J. S. J. Org. Chem. 2017, 82, 2276.
doi: 10.1021/acs.joc.6b03059 pmid: 28164699 |
[22] |
(a) Mengel, A.; Reiser, O. Chem. Rev. 1999, 99, 1191.
pmid: 11749444 |
(b) Evans, D. A.; Siska, S. J.; Cee, V. J. Angew. Chem., Int. Ed. 2003, 42, 1761.
doi: 10.1002/anie.200350979 pmid: 11749444 |
|
(c) Cee, V. J.; Cramer, C. J.; Evans, D. A. J. Am. Chem. Soc. 2006, 128, 2920.
doi: 10.1021/ja0555670 pmid: 11749444 |
|
[23] |
Yang, M.; Chen, C.; Yi, X.; Li, Y.; Wu, X.; Li, Q.; Ban, S. Org. Biomol. Chem. 2019, 17, 2883.
doi: 10.1039/C9OB00330D |
[24] |
Li, Feng.; Wang, J.; Pei, W.; Ma, H.; Li, H.; Cui, M.; Peng, S.; Wang, S.; Liu, L. Tetrahedron Lett. 2018, 59, 3010.
doi: 10.1016/j.tetlet.2018.06.062 |
[25] |
Trost, B. M.; Joey Hung, C.-I.; Scharf, M. J. Angew. Chem., Int. Ed. 2018, 57, 11408.
doi: 10.1002/anie.v57.35 |
[26] |
Huang, Z-Y.; Yang, H.; Zhou, L.; Li, Q.-H.; Zhao, Z.-G. Tetrahedron. 2022, 112, 132740.
doi: 10.1016/j.tet.2022.132740 |
[27] |
Wu, Bo.; Yu, Z.; Gao, X.; Lan, Y.; Zhou, Y.-G. Angew. Chem., Int. Ed. 2017, 56, 4006.
doi: 10.1002/anie.201700437 pmid: 28247568 |
[28] |
(a) Green, A. G.; Liu, P.; Merlic, C. A.; Houk, K. N. J. Am. Chem. Soc. 2014, 136, 4575.
doi: 10.1021/ja411699u |
(b) Wang, T.; Yu, Z.; Hoon, D. L.; Phee, C. Y.; Lan, Y.; Lu, Y. J. Am. Chem. Soc. 2016, 138, 265.
doi: 10.1021/jacs.5b10524 |
|
[29] |
Wang, Y.-N.; Xiong, Q.; Lu, L.-Q.; Zhang, Q.-L.; Wang, Y.; Lan, Y.; Xiao, W.-J. Angew. Chem., Int. Ed. 2019, 58, 11013.
doi: 10.1002/anie.v58.32 |
[30] |
Xu, Y.-W.; Hu, X.-P. Org. Lett. 2019, 21, 8091.
doi: 10.1021/acs.orglett.9b03081 |
[31] |
Hattori, G.; Sakata, K.; Matsuzawa, H.; Tanabe, Y.; Miyake, Y.; Nishibayashi, Y. J. Am. Chem. Soc. 2010, 132, 10592.
doi: 10.1021/ja1047494 pmid: 20617844 |
[32] |
Zhao, J.-Q.; Luo, S.-W.; Zhang, X.-M.; Xu, X.-Y.; Zhou, M.-Q.; Yuan, W.-C. Tetrahedron 2017, 73, 5444.
doi: 10.1016/j.tet.2017.07.053 |
[33] |
Sharma, B. M.; Shinde, D. R.; Jain, R.; Begari, E.; Satbhaiya, S.; Gonnade, R. G.; Kumar, P. Org. Lett. 2018, 20, 2787.
doi: 10.1021/acs.orglett.8b00745 |
[34] |
Masuyama, Y.; Kobayashi, Y.; Yanagi, R.; Kurusu, Y. Chem. Lett. 1992, 2039.
|
[35] |
Isambert, N.; Cruz, M.; Arévalo, M. J.; Gómez, E.; Lavilla, R. Org. Lett. 2007, 9, 4199.
pmid: 17867693 |
[36] |
Huo, C.; Yuan, Yong. J. Org. Chem. 2015, 80, 12704.
doi: 10.1021/acs.joc.5b02354 |
[37] |
Huo, C.; Yuan, Y.; Chen, F.; Tang, J.; Wang, Y. Org. Lett. 2015, 17, 4208.
doi: 10.1021/acs.orglett.5b01985 |
[38] |
Zhou, H.; Yang, X.; Li, S.; Zhu, Y.; Li, Y.; Zhang, Y. Org. Biomol. Chem. 2018, 16, 6728.
doi: 10.1039/C8OB01844H |
[39] |
(a) For reviews on nitrosocarbonyl chemistry, see: Palmer, L. I.; Frazier, C. P.; Read De Alaniz, J. Synthesis 2014, 46, 269.
doi: 10.1055/s-00000084 |
(b) Maji, B.; Yamamoto, H. Bull. Chem. Soc. Jpn. 2015, 88, 753.
doi: 10.1246/bcsj.20150040 |
|
(c) Memeo, M. G.; Quadrelli, P. Chem. Rev. 2017, 117, 2108.
doi: 10.1021/acs.chemrev.6b00684 |
|
(d) Dana, S.; Ramakrishna, I.; Baidya, M. Synthesis 2017, 49, 3281.
doi: 10.1055/s-0036-1590793 |
|
[40] |
Mallik, S.; Bhajammanavar, V.; Baidya, M. Org. Lett. 2020, 22, 1437.
doi: 10.1021/acs.orglett.0c00039 |
[41] |
(a) Payette, J. N.; Yamamoto, H. J. Am. Chem. Soc. 2008, 130, 12276.
doi: 10.1021/ja804325f pmid: 18722431 |
(b) Maji, B.; Yamamoto, H. Angew. Chem., Int. Ed. 2014, 53, 14472.
doi: 10.1002/anie.201408893 pmid: 18722431 |
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