Engineering Biomass Feedstock Cyrene to Value-Added Compounds by Enaminone Platform Construction

doi:10.6023/cjoc202212002

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (6): 2096-2103.DOI: 10.6023/cjoc202212002 Previous Articles Next Articles

烯胺酮平台构建转化生物质产品Cyrene为增值化合物

黄丽珠^a, 刘云云^a^,^*(), 万结平^a^,^b^,^*()

a 江西师范大学化学化工学院国家单糖化学合成工程技术研究中心南昌 330022
b 南京林业大学林产化学与材料国际创新高地南京 210037

收稿日期:2022-12-03 修回日期:2023-01-06 发布日期:2023-01-18
基金资助:
国家自然科学基金(22161022)

Engineering Biomass Feedstock Cyrene to Value-Added Compounds by Enaminone Platform Construction

Lizhu Huang^a, Yunyun Liu^a,*(), Jieping Wan^a^,^b,*()

a National Engineering Research Center for Carbohydrate Synthesis, College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330022
b International Innovation Center for Forest Chemicals and Materials, Nanjing Forestry University, Nanjing 210037

Received:2022-12-03 Revised:2023-01-06 Published:2023-01-18
Contact: * E-mail: chemliuyunyun@jxnu.edu.cn; wanjieping@jxnu.edu.cn
Supported by:
National Natural Science Foundation of China(22161022)

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Abstract

The enamination of Cyrene in the ketone α-site leading to the enamino Cyrene (EC) has been developed. The practical preparation of EC as a platform synthon opens broad space of chemical transformation for Cyrene biomass feedstock in the synthesis of diverse value-added chemicals. In the present work, the transformation of the EC for the synthesis of many different chiral organic derivatives, including NH-/N,N-disubstituted ECs, the cyanoalkenyl- and vinyl phosphine oxide-elabo- rated Cyrene, Cyrene fused furan, and 2,2-difluorodihydrofuran fused Cyrene, has been realized.

Key words: Cyrene, biomass feedstock, enamination, platform, value-added

Cite this article

Lizhu Huang, Yunyun Liu, Jieping Wan. Engineering Biomass Feedstock Cyrene to Value-Added Compounds by Enaminone Platform Construction[J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2096-2103.

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References 19

[1]	(a) Sherwood, J.; De bruyn, M.; Constantinou, A.; Moity, L.; McElroy, C. R.; Farmer, T. J.; Duncan, T.; Raverty, W.; Hunt, A. J.; Clark, J. H. Chem. Commun. 2014, 50, 9650. doi: 10.1039/C4CC04133J pmid: 19533728
	(b) Craythorne, S. J.; Anderson, K.; Lorenzini, F.; McCausland, C.; Smith, E. F.; Licence, P.; Marr, A. C.; Marr, P. C. Chem.-Eur. J. 2009, 15, 7094. doi: 10.1002/chem.200801809 pmid: 19533728
	(c) De bruyn, M.; Fan, J.; Budarin, V. L.; Macquarrie, D. J.; Gomez, L. D.; Simister, R.; Farmer, T. J.; Raverty, W. D.; McQueen-Mason, S. J.; Clark, J. H. Energy Environ. Sci. 2016, 9, 2571. doi: 10.1039/C6EE01352J pmid: 19533728
	(d) Miura, M.; Kaga, H.; Yoshida, T.; Ando, K. J. Wood Sci. 2001, 47, 502. doi: 10.1007/BF00767906 pmid: 19533728
	(e) Sui, X.-W.; Wang, Z.; Liao, B.; Zhang, Y.; Guo, Q.-X. Bioresour. Technol. 2012, 103, 466. doi: 10.1016/j.biortech.2011.10.010 pmid: 19533728
[2]	See also information in Merck product introduction: https://www.merckgroup.com/en/research/science-space/envisioning-tomorrow/scarcity-of-resources/cyrene.html.
[3]	Camp, J. E. ChemSusChem 2018, 11, 3048. doi: 10.1002/cssc.201801420
[4]	(a) Duval, A.; Avérous, L. Green Chem. 2022, 24, 338. doi: 10.1039/D1GC03395F
	(b) Meng, X.; Pu, Y.; Li, M.; Ragauskas, A. J. Green Chem. 2020, 22, 2862. doi: 10.1039/D0GC00661K
	(c) Marathianos, A.; Liarou, E.; Hancox, E.; Grace, J. L.; Lester, D. W.; Haddleton, D. M. Green Chem. 2020, 22, 5833. doi: 10.1039/D0GC02184A
	(d) Gao, F.; Bai, R.; Ferlin, F.; Vaccaro, L.; Li, M.; Gu, Y. Green Chem. 2020, 22, 6240. doi: 10.1039/D0GC02149K
	(e) Brouwer, T.; Schuur, B. ACS Sustainable Chem. Eng. 2020, 8, 14807. doi: 10.1021/acssuschemeng.0c04159
[5]	(a) Bousfield, T. W.; Pearce, K. P. R.; Nyamini, S. B.; Angelis-Dimakis, A.; Camp, J. E. Green Chem. 2019, 21, 3675. doi: 10.1039/C9GC01180C
	(b) Mistry, L.; Mapesa, K.; Bousfield, T. W.; Jason, E. C. Green Chem. 2017, 19, 2123 doi: 10.1039/C7GC00908A
[6]	Yu, H.; Yu, D.; Xue, Z.; Zhang, B.; Mu, T. Chem. Eng. J. 2022, 431, 133397. doi: 10.1016/j.cej.2021.133397
[7]	(a) Wilson, K. L.; Kennedy, A. R.; Murray, J.; Greatrex, B.; Jamieson, C.; Watson, A. J. B. Beilstein J. Org. Chem. 2016, 12, 2005. doi: 10.3762/bjoc.12.187
	(b) Wilson, K. L.; Murray, J.; Jamieson, C.; Watson, A. J. B. Synlett 2018, 29, 650. doi: 10.1055/s-0036-1589143
[8]	Mention, M. M.; Flourat, A. L.; Peyrot, C.; Allais, F. Green Chem. 2020, 22, 2077. doi: 10.1039/D0GC00122H
[9]	Gonzalo, G. Biocatal. Biotransfor. 2022, 40, 252. doi: 10.1080/10242422.2021.1887150
[10]	Tamargo, R. J. I.; Rubio, P. Y. M.; Mohandoss, S.; Shim, J.-J.; Lee, Y. R. ChemSusChem 2021, 14, 2133. doi: 10.1002/cssc.v14.9
[11]	Ray, P.; Hughes, T.; Smith, C.; Hibbert, M.; Saito, K.; Simon, G. P. Polym. Chem. 2019, 10, 3334. doi: 10.1039/C9PY00353C pmid: 32237202
	(b) Diot-Néant, F.; Mouterde, L.; Fadlallah, S.; Miller, S. A.; Allais, F. ChemSusChem 2020, 13, 2613. doi: 10.1002/cssc.202000680 pmid: 32237202
[12]	De bruyn, M.; Budarin, V. L.; Misefari, A.; Shimizu, S.; Fish, H.; Cockett, M.; Hunt, A. J.; Hofsteffter, H.; Weckhuysen, B. M.; Clark, J. H.; Macquarrie, D. J. ACS Sustainable Chem. Eng. 2019, 7, 7878. doi: 10.1021/acssuschemeng.9b00470
[13]	Bonneau, G.; Peru, A. A. M.; Flourat, A. L.; Allais, F. Green Chem. 2018, 20, 2455. doi: 10.1039/C8GC00553B
[14]	Krishna, S. H.; McClelland, D. J.; Rashke, Q. A.; Dumesic, J. A.; Huber, G. W. Green Chem. 2017, 19, 1278. doi: 10.1039/C6GC03028A
[15]	Hughes, L.; McElroy, C. R.; Whitwood, A. C.; Hunt, A. J. Green Chem. 2018, 20, 4423. doi: 10.1039/C8GC01227J
[16]	Alhifthi, A.; Harris, B. L.; Goerigk, L.; White, J. M.; Williams, S. J. Org. Biomol. Chem. 2017, 15, 10105. doi: 10.1039/c7ob02499a pmid: 29170781
[17]	(a) Wang, Z.; Zhao, B.; Liu, Y.; Wan, J.-P. Adv. Synth. Catal. 2022, 364, 1508. doi: 10.1002/adsc.v364.9
	(b) Zheng, X.; Liu, Y.; Wan, J.-P. Chin. J. Org. Chem. 2021, 41, 2700. doi: 10.6023/cjoc202104053
	(c) Guo, H.; Liu, Y.; Wen, C.; Wan, J.-P. Green Chem. 2022, 24, 5058. doi: 10.1039/D2GC01644C
	(c) Fu, L.; Xu, W.; Pu, M.; Wu, Y-D.; Liu, Y.; Wan, J.-P. Org. Lett. 2022, 24, 3003. doi: 10.1021/acs.orglett.2c00912
	(d) Guo, Y.; Liu, Y.; Wan, J.-P. Chin. Chem. Lett. 2022, 33, 855. doi: 10.1016/j.cclet.2021.08.003
	(d) Yu, Q.; Liu, Y.; Wan, J.-P. Chin. Chem. Lett. 2021, 32, 3514. doi: 10.1016/j.cclet.2021.04.037
	(e) Duan, X.; Li, H.; Li, W.; Wang, J.; Liu, N. ChemistrySelect 2021, 6, 6478. doi: 10.1002/slct.v6.25
	(f) Zhang, B.; Fu, Z.; Yang, H.; Liu, D.; Sun, Y.; Xu, Y.; Yu, F.; Yan, S. Adv. Synth. Catal. 2022, 364, 1602. doi: 10.1002/adsc.v364.9
	(g) Fu, R.; Liu, Y.; Wu, T.; Zhang, X.; Zhu, Y.; Luo, J.; Zhang, Z.; Jiang, Y. Chem. Commun. 2022, 58, 3525. doi: 10.1039/D2CC00169A
	(h) Wu, Y.; Du, J.; Hao, W.; Jiang, B. Chin. J. Org. Chem. 2021, 41, 1563. (in Chinese) doi: 10.6023/cjoc202102018
	(吴亚男, 杜建宇, 郝文娟, 姜波, 有机化学, 2021, 41, 1563.) doi: 10.6023/cjoc202102018
	(i) Xie, Y.-Y.; Wang, Y.-C.; Qu, H.-E.; Tan, X.-C.; Wang, H.-S.; Pan, Y.-M. Adv. Synth. Catal. 2014, 356, 3347. doi: 10.1002/adsc.201400315
[18]	CCDC 2201314 and 2201818 contain the crystallographic data associated with this work.
[19]	The relative configuration of the chiral centres in products 8 and 9 were assigned by NOE NMR analysis.

烯胺酮平台构建转化生物质产品Cyrene为增值化合物

Engineering Biomass Feedstock Cyrene to Value-Added Compounds by Enaminone Platform Construction

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References 19

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Entry	Solvent	Time/h	T/℃	Yield^b/%
1	p-Xylene	6	100	32
2	Toluene	6	100	84
3	THF	6	100	66
4	DMF	6	100	n.r
5	EL	6	100	n.r
6	EtOH	6	100	n.r
7	i-PrOH	6	100	n.r
8	DMSO	6	100	n.r
9	Acetone	6	100	n.r
10	1,4-Dioxane	6	100	n.r
11	NMP	6	100	n.r
12	MeCN	6	100	n.r
13	Toluene	5	100	87
14	Toluene	4	100	89
15	Toluene	3	100	56
16	Toluene	4	110	77
17	Toluene	4	90	83
18	Toluene	4	80	53

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