SIOC English
有机化学
高级检索

有机化学 >

2022 , Vol. 42 >Issue 6: 1747 - 1758

DOI: https://doi.org/10.6023/cjoc202112040

研究论文

Ir-BiphPHOX催化的不对称氢化反应合成手性5-芳基噁唑烷-2-酮

  • 张同利 ,
  • 晏君 ,
  • 何敬立 ,
  • 寇学振 ,
  • 申杰峰 ,
  • 刘德龙 ,
  • 张万斌
展开
  • a 上海交通大学药学院 上海市手性药物分子工程重点实验室 上海 200240
    b 上海交通大学化学化工学院 教育部变革性分子前沿科学中心 上海 200240

收稿日期: 2021-12-29

  修回日期: 2022-02-21

  网络出版日期: 2022-03-03

基金资助

国家自然科学基金(21672142); 国家自然科学基金(21971162); 国家自然科学基金(21831005); 国家自然科学基金(21620102003); 上海市“超级博士后”激励计划(2020230); 中国博士后科学基金(2020M681276)

收起

Synthesis of Chiral 5-Aryl-2-oxazolidinones via an Ir-BiphPHOX Catalyzed Enantioselective Hydrogenation

  • Tongli Zhang ,
  • Jun Yan ,
  • Jingli He ,
  • Xuezhen Kou ,
  • Jiefeng Shen ,
  • Delong Liu ,
  • Wanbin Zhang
Expand
  • a Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Pharmacy, Shanghai Jiao Tong University, Shanghai 200240
    b Frontiers Science Center for Transformative Molecules, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240
*E-mail: ;

Received date: 2021-12-29

  Revised date: 2022-02-21

  Online published: 2022-03-03

Supported by

National Natural Science Foundation of China(21672142); National Natural Science Foundation of China(21971162); National Natural Science Foundation of China(21831005); National Natural Science Foundation of China(21620102003); Shanghai Post-Doctoral Excellence Program(2020230); China Postdoctoral Science Foundation(2020M681276)

Fold

摘要

利用轴手性Ir-BiphPHOX催化剂, 首次实现了5-芳基噁唑-2-酮的不对称催化氢化反应, 高收率、高选择性地合成了一系列手性5-芳基噁唑烷-2-酮类化合物. 该反应对多种官能团具有良好的相容性, 所得产物经简单转化可得到多种手性氨基醇类化合物或可衍生出具有生物活性的手性杂环化合物.

关键词： BiphPHOX; 不对称氢化; 5-芳基噁唑烷-2-酮; 手性; Ir-催化氢化

本文引用格式

张同利 , 晏君 , 何敬立 , 寇学振 , 申杰峰 , 刘德龙 , 张万斌 . Ir-BiphPHOX催化的不对称氢化反应合成手性5-芳基噁唑烷-2-酮[J]. 有机化学, 2022 , 42(6) : 1747 -1758 . DOI: 10.6023/cjoc202112040

Abstract

The enantioselective catalytic hydrogenation of 5-aryl-2-oxazolones has been achieved for the first time using the axially chiral Ir-BiphPHOX catalyst, providing the corresponding chiral 5-aryl-2-oxazolidinones in high yields and with excellent enantioselectivities. The protocol has good compatibility with a variety of functional groups, and the resulting products can be converted into various chiral amino alcohol compounds or can be transformed into a series of chiral heterocyclic compounds with various biological activities.

Key words： BiphPHOX; enantioselective hydrogenation; 5-aryl-2-oxazolidinone; chirality; Ir-catalyzed hydrogenation

参考文献

[1]
(a) Barbachyn, M. R.; Ford, W. Angew. Chem., Int. Ed. 2003, 42, 2010.
[1]
(b) Mukhtar, T. A.; Wright, G. D. Chem. Rev. 2005, 105, 529.
[1]
(c) Wan, Y.-D.; Chen, Z.-X.; Yang, G.-C. Chin. J. Org. Chem. 2005, 25, 1039. (in Chinese)
[1]
( 万亚东, 陈祖兴, 杨桂春, 有机化学, 2005, 25, 1039.)
[1]
(d) Rensol, A. R.; Luehr, G. W.; Gordeev, M. F. Bioorg. Med. Chem. 2006, 14, 4227.
[1]
(e) Zappia, G.; Menendez, P.; Misiti, D.; Nevola, L.; Botta, B. Mini-Rev. Med. Chem. 2007, 7, 389.
[1]
(f) Das, B.; Rudra, S.; Yadav, A.; Ray, A.; Pandya, M.; Rattan, A.; Mehta, A. Bioorg. Med. Chem. Lett. 2009, 19, 6424.
[1]
(g) Liang, F.; Chen, L.; Xing, G. Chin. J. Org. Chem. 2009, 29, 1317. (in Chinese)
[1]
( 梁芬芬, 陈力, 邢国文, 有机化学, 2009, 29, 1317.)
[1]
(h) Shaw, K. J.; Barbachyn, M. R. Ann. N. Y. Acad. Sci. 2011, 1241, 48.
[1]
(i) Zhang, H.-Z.; Zhou, C.-H.; Geng, R.-X.; Ji, Q.-G. Chin. J. Org. Chem. 2011, 31, 1963. (in Chinese)
[1]
( 张慧珍, 周成合, 耿蓉霞, 吉庆刚, 有机化学, 2011, 31, 1963.)
[2]
Fujimoto, J.; Okamoto, R.; Noguchi, N. J. Med. Chem. 2017, 60, 8963.
[3]
Slassi, A.; Joseph, B.; Ma, F.; Egle, I.; Clayton, I.; Isaac, M.; Swierczek, K. US 20070275966, 2007.
[4]
(a) Onodera, G.; Watabe, K.; Matsubara, M.; Oda, K.; Kezuka, S.; Takeuchia, R. Adv. Synth. Catal. 2008, 350, 2725.
[4]
(b) Li, W.; Wollenburg, M.; Glorius, F. Chem. Sci. 2018, 9, 6260.
[5]
Han, X.; Liu, R.; Ji, L. J. Chromatogr. B 2016, 1008, 108.
[6]
Lu, C.; Luo, Z.; Huang, L. Tetrahedron: Asymmetry 2011, 22, 722.
[7]
Wei, S.; Messerer, R.; Tsogoeva, S. B. Chem.-Eur. J. 2011, 17, 14380.
[8]
For selected examples: (a) Puschin, N. A.; Mitic, R. V. Leibigs Ann. Chem. 1937, 532, 300.
[8]
(b) Newma, M. S.; Kutner, A. J. Am. Chem. Soc. 1951, 73, 4199.
[8]
(c) Ben, I. D. J. Am. Chem. Soc. 1956, 78, 4962.
[8]
(d) Dyen, M. E.; Swern, D. Chem. Rev. 1967, 67, 197.
[8]
(e) Yoshida, T.; Kambe, N.; Murai, S.; Sonoda, N. Tetrahedron Lett. 1986, 27, 3037.
[8]
(f) Pridgen, L. N.; Prol, J.; Alexander, B. J. Org. Chem. 1989, 54, 3231.
[8]
(g) Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835.
[8]
(h) Kudo, N.; Taniguchi, M.; Furuta, S.; Sato, K.; Endo, T.; Honma, T. J. Agric. Food Chem. 1998, 46, 5305.
[8]
(i) Cynamon, M. H.; Klemens, S. P.; Sharpe, C. A.; Chase, S. Antimicrob. Agents Chemother. 1999, 43, 1189.
[8]
(j) Wang, G.; Hollingsworth, R. I. Tetrahedron: Asymmetry 2000, 11, 4429.
[8]
(k) Gabriele, B.; Salerno, G.; Costa, M.; Chiusoli, G. P. Org. Lett. 2000, 2, 625.
[8]
(l) Ariza, X.; Pineda, O.; Urpi, F.; Vilarrasa, J. Tetrahedron Lett. 2001, 42, 4995.
[8]
(m) Liu, J. M.; Peng, X. G.; Liu, J. H.; Zheng, S. Z.; Sun, W.; Xia, C. G. Tetrahedron Lett. 2007, 48, 929.
[8]
(n) Patil, Y. P.; Tambade, P. J.; Jagtap, S. R.; Bhanage, B. M. J. Mol. Catal. A: Chem. 2008, 289, 14.
[9]
(a) Iwama, S.; Katsumura, S. Bull. Chem. Soc. Jpn. 1994, 67, 3363.
[9]
(b) Tingoli, M.; Testaferri, L.; Temparini, A.; Tiecco, M. J. Org. Chem. 1996, 61, 7085.
[9]
(c) Ueno, A.; Kayaki, Y.; Ikariya, T. Green Chem. 2013, 15, 425.
[9]
(d) Khan, A.; Xing, J.; Zhao, J.; Kan, Y.; Zhang, W.; Zhang, Y. J. Chem.-Eur. J. 2015, 21, 120.
[10]
(a) Lebal, H.; Huard, K.; Lectard, S. J. Am. Chem. Soc. 2005, 127, 14198.
[10]
(b) Barman, D. N.; Nicholas, K. M. Eur. J. Org. Chem. 2011, 2011, 908.
[11]
Wan, N. W.; Tian, J. W.; Zhou, X. Y.; Wang, H. H.; Cui, B. D.; Han, W. Y.; Chen, Y. Z. Adv. Synth. Catal. 2019, 361, 4651.
[12]
(a) Noyori, R.; Takaya, H. Acc. Chem. Res. 1990, 23, 345.
[12]
(b) Tang, W.; Zhang, X. Chem. Rev. 2003, 103, 3029.
[12]
(c) Johnson, N. B.; Lennon, I. C.; Moran, P. H.; Raasden, J. Acc. Chem. Res. 2007, 40, 1291.
[12]
(d) Ma, Y.-H.; Zhang, Y.-J.; Zhang, W.-B. Chin. J. Org. Chem. 2007, 27, 289. (in Chinese)
[12]
( 马元辉, 张勇健, 张万斌, 有机化学, 2007, 27, 289.)
[12]
(e) Li, Y.; Zheng, Y.; Tian, F.; Zhang, Y.; Zhang, W. Chin. J. Org. Chem. 2009, 29, 1487. (in Chinese)
[12]
( 李亚玺, 郑玉林, 田丰涛, 张勇健, 张万斌, 有机化学, 2009, 29, 1487.)
[12]
(f) Xie, J. H.; Zhu, S. F.; Zhou, Q. L. Chem. Rev. 2011, 111, 1713.
[12]
(g) Verendel, J. J.; Pamies, O.; Dieguez, M.; Andersson, P. G. Chem. Rev. 2014, 114, 2130.
[12]
(h) Xie, J.; Zhou, Q. Acta Chim. Sinica 2014, 72, 778. (in Chinese)
[12]
( 谢建华, 周其林, 化学学报, 2014, 72, 778.)
[12]
(i) Wang, Y.; Zhang, Z.; Zhang, W. Chin. J. Org. Chem. 2015, 35, 528. (in Chinese)
[12]
( 王英杰, 张振锋, 张万斌, 有机化学, 2015, 35, 528.)
[12]
(j) Yuan, Q.; Zhang, W. Chin. J. Org. Chem. 2016, 36, 274. (in Chinese)
[12]
( 袁乾家, 张万斌, 有机化学, 2016, 36, 274.)
[12]
(k) Wang, Z.; Zhang, Z.; Liu, Y.; Zhang, W. Chin. J. Org. Chem. 2016, 36, 447. (in Chinese)
[12]
( 王志惠, 张振锋, 刘燕刚, 张万斌, 有机化学, 2016, 36, 447.)
[12]
(l) Zhang, Z.; Butt, N. A.; Zhang, W. Chem. Rev. 2016, 116, 14769.
[12]
(m) Wiesenfeldt, M. P.; Nairoukh, Z.; Dalton, T.; Glorius, F. Angew. Chem., Int. Ed. 2019, 58, 10460.
[12]
(n) Gu, X.; Li, X.; Xie, J.; Zhou, Q. Acta Chim. Sinica 2019, 77, 598. (in Chinese)
[12]
( 顾雪松, 李校根, 谢建华, 周其林, 化学学报, 2019, 77, 598.)
[12]
(o) Dou, X.; Liu, D.; Zhang, W. Chin. J. Pharm. 2020, 51, 145. (in Chinese)
[12]
( 窦骁勇, 刘德龙, 张万斌, 中国医药工业杂志, 2020, 51, 145.)
[12]
(p) Chen, J.; Zhang, W. Chin. J. Org. Chem. 2020, 40, 4372. (in Chinese)
[12]
( 陈建中, 张万斌, 有机化学, 2020, 40, 4372.)
[12]
(q) Zheng, Y.; Zhang, X.; Zhang, R.; Ma, B. Green Synth. Catal. 2021, 2, 393.
[13]
Wang, Q.; Tan, X.; Zhu, Z.; Dong, X. Q.; Zhang, X. Tetrahedron Lett. 2016, 57, 658.
[14]
Li, W.; Wollenburg, M.; Glorius, F. Chem. Sci. 2018, 9, 6260.
[15]
Liu, Y.; Yi, Z.; Yang, X.; Wang, H.; Yin, C.; Wang, M.; Dong, X. Q.; Zhang, X. ACS Catal. 2020, 10, 11153.
[16]
(a) Tian, F.; Yao, D.; Zhang, Y. J.; Zhang, W. Tetrahedron 2009, 65, 9609.
[16]
(b) Tian, F.; Yao, D.; Liu, Y.; Xie, F.; Zhang, W. Adv. Synth. Catal. 2010, 352, 1841.
[16]
(c) Liu, Y.; Yao, D.; Li, K.; Tian, F.; Xie, F.; Zhang, W. Tetrahedron 2011, 67, 8445.
[16]
(d) Liu, Y.; Zhang, W. Angew. Chem., Int. Ed. 2013, 52, 2203.
[16]
(e) Liu, Y.; Gridnev, I. D.; Zhang, W. Angew. Chem., Int. Ed. 2014, 53, 1901.
[16]
(f) Xia, J.; Yang, G.; Zhuge, R.; Liu, Y.; Zhang, W. Chem. Eur. J. 2016, 22, 18354.
[16]
(g) Quan, M.; Tang, L.; Shen, J.; Yang, G.; Zhang, W. Chem. Commun. 2017, 53, 609.
[16]
(h) Xia, J.; Nie, Y.; Yang, G.; Liu, Y.; Zhang, W. Org. Lett. 2017, 19, 4884.
[16]
(i) Meng, K.; Xia, J.; Wang, Y.; Zhang, X.; Yang, G.; Zhang, W. Org. Chem. Front. 2017, 4, 1601.
[16]
(j) Xia, J.; Nie, Y.; Yang, G.; Liu, Y.; Gridnev, I. D.; Zhang, W. Chin. J. Chem. 2018, 36, 612.
[16]
(k) Wang, Y.; Xia, J.; Yang, G.; Zhang, W. Tetrahedron 2018, 74, 477.
[16]
(l) Yan, J.; Nie, Y.; Gao, F.; Yuan, Q.; Xie, F.; Zhang, W. Tetrahedron 2021, 84, 132003.
[16]
(m) Nie, Y.; Li, J.; Yan, J.; Yuan, Q.; Zhang, W. Org. Lett. 2021, 23, 5373.
[17]
Tobias, A.; Goran, H. Org. Lett. 2009, 11, 503.
Options
文章导航

/

〈 〉