SIOC English
有机化学
高级检索

有机化学 >

2023 , Vol. 43 >Issue 8: 2926 - 2933

DOI: https://doi.org/10.6023/cjoc202303021

研究论文

铑催化2-烯基苯酚与炔烃的对映体选择性螺环化反应

  • 张素珍 ,
  • 张文文 ,
  • 杨慧 ,
  • 顾庆 ,
  • 游书力
展开
  • a 上海理工大学材料与化学学院 上海 200093
    b 中国科学院上海有机化学研究所 金属有机化学国家重点实验室 上海 200032

收稿日期: 2023-03-15

  修回日期: 2023-03-28

  网络出版日期: 2023-04-10

基金资助

国家自然科学基金(21821002); 国家自然科学基金(92256302); 国家自然科学基金(22071260)

收起

Rhodium-Catalyzed Enantioselective Spiroannulation of 2-Alkenylphenols with Alkynes

  • Suzhen Zhang ,
  • Wenwen Zhang ,
  • Hui Yang ,
  • Qing Gu ,
  • Shuli You
Expand
  • a School of Material and Chemistry, University of Shanghai for Science and Technology, Shanghai 200093
    b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032
*E-mail: ,

Received date: 2023-03-15

  Revised date: 2023-03-28

  Online published: 2023-04-10

Supported by

The National Natural Science Foundation of China(21821002); The National Natural Science Foundation of China(92256302); The National Natural Science Foundation of China(22071260)

Fold

摘要

发展了铑催化2-烯基苯酚与炔烃的对映选择性螺环化反应. 在5 mol% 1,1'-联二萘酚(BINOL)衍生的环戊二烯铑络合物[(R)-CpRh1]和2 equiv.的醋酸铜存在下, C—H活化/螺环化反应可以高达84%收率和81% ee对映选择性获得手性螺环己烯酮化合物. 该反应条件温和, 具有良好的官能团耐受性.

关键词： 2-烯基苯酚; 炔烃; 环戊二烯铑络合物; 螺环化反应; 螺环己烯酮

本文引用格式

张素珍 , 张文文 , 杨慧 , 顾庆 , 游书力 . 铑催化2-烯基苯酚与炔烃的对映体选择性螺环化反应[J]. 有机化学, 2023 , 43(8) : 2926 -2933 . DOI: 10.6023/cjoc202303021

Abstract

Rh-catalyzed enantioselective spiroannulation of 2-alkenylphenols with alkynes was developed. In the presence of 5 mol% BINOL-derived (BINOL: 1,1'-bi-2,2'-naphthol) cyclopentadiene-Rh complex [(R)-CpRh1] and 2 equiv. of Cu(O- Ac)2, the C—H activation/annulation reaction proceeded smoothly to afford a wide range of enantioenriched spirocyclohexenones in up to 84% yield and 81% ee. This reaction features mild reaction conditions and good functional group tolerance.

Key words： 2‑alkenylphenol; alkyne; cyclopentadiene-Rh complex; spiroannulation; spirocyclohexenone

参考文献

[1]
For reviews on transition-metal-catalyzed C—H activation/annul- ation reactions, see: (a) Satoh, T.; Miura, M. Chem.-Eur. J. 2010, 16, 11212.
[1]
(b) Ackermann, L. Acc. Chem. Res. 2014, 47, 281.
[1]
(c) Yang, Y.; Li, K.; Cheng, Y.; Wan, D.; Li, M.; You, J. Chem. Commun. 2016, 52, 2872.
[1]
(d) Duarah, G.; Kaishap, P. P.; Begum, T.; Gogoi, S. Adv. Synth. Catal. 2019, 361, 654.
[1]
(d) Kuang, G.; Liu, G.; Zhang, X.; Lu, N.; Peng, Y.; Xiao, Q.; Zhou, Y. Synthesis 2020, 52, 993.
[1]
(e) Saha, A.; Shankar, M.; Sau, S.; Sahoo, A. K. Chem. Commun. 2022, 58, 4561.
[1]
Selected reviews on transition-metal-catalyzed C—H functionalizations, see: (f) Ji, Y.; Zhang, M.; Xing, M.; Cui, H.; Zhao, Q.; Zhang, C. Chin. J. Chem. 2021, 39, 391.
[1]
(g) Liu, X.; Kuang, C.; Su, C. Acta Chim. Sinica 2022, 80, 1135. (in Chinese)
[1]
( 刘霞, 匡春香, 苏长会, 化学学报, 2022, 80, 1135.)
[1]
(h) Gu, H.; Jin, X.; Li, J.; Li, H.; Liu, J. Chin. J. Org. Chem. 2022, 42, 2682. (in Chinese)
[1]
( 顾海春, 靳新新, 李嘉琪, 李贺, 刘景林, 有机化学, 2022, 42, 2682.)
[2]
(a) Reddy Chidipudi, S.; Khan, I.; Lam, H. W. Angew. Chem., Int. Ed. 2012, 51, 12115.
[2]
(b) Dooley, J. D.; Reddy Chidipudi, S.; Lam, H. W. J. Am. Chem. Soc. 2013, 135, 10829.
[2]
(c) Reddy Chidipudi, S.; Burns, D. J.; Khan, I.; Lam, H. W. Angew. Chem., Int. Ed. 2015, 54, 13975.
[3]
(a) Nan, J.; Zuo, Z.; Luo, L.; Bai, L.; Zheng, H.; Yuan, Y.; Liu, J.; Luan, X.; Wang, Y. J. Am. Chem. Soc. 2013, 135, 17306.
[3]
(b) Han, L.; Wang, H.; Luan, X. Org. Chem. Front. 2018, 5, 2453.
[3]
(c) Hao, J.; Ge, Y.; Yang, L.; Wang, J.; Luan, X. Tetrahedron Lett. 2021, 71, 153050.
[3]
(d) Li, K.; Bai, L.; Luan, X. Chin. J. Org. Chem. 2019, 39, 2211. (in Chinese)
[3]
( 李锟雨, 白璐, 栾新军, 有机化学, 2019, 39, 2211.)
[3]
(e) Li, H.; Cui, X. Chin. J. Org. Chem. 2020, 40, 543. (in Chinese)
[3]
( 李欢, 崔秀灵, 有机化学, 2020, 40, 543.)
[4]
(a) Zheng, J.; Wang, S.-B.; Zheng, C.; You, S.-L. J. Am. Chem. Soc. 2015, 137, 4880.
[4]
(b) Zheng, C.; Zheng, J.; You, S.-L. ACS Catal. 2016, 6, 262.
[5]
Other examples of enantioselective C—H spiroannulation reactions with alkynes, see: (a) Zhang, M.; Huang, G. Chem. Eur. J. 2016, 22, 9356.
[5]
(b) Zheng, J.; Wang, S.-B.; Zheng, C.; You, S.-L. Angew. Chem., Int. Ed. 2017, 56, 4540.
[5]
(c) Duarah, G.; Kaishap, P. P.; Sarma, B.; Gogoi, S. Chem. Eur. J. 2018, 24, 10196.
[5]
(d) Li, H.; Gontla, R.; Flegel, J.; Merten, C.; Ziegler, S.; Antonchick, A. P.; Waldmann, H. Angew. Chem., Int. Ed. 2019, 58, 307.
[5]
(e) Huang, Y.-Q.; Wu, Z.-J.; Zhu, L.; Gu, Q.; Lu, X.; You, S.-L.; Mei, T.-S. CCS Chem. 2022, 4, 3181.
[5]
(f) Wang, Y.; Huang, X.; Wang, Q.; Tang, Y.; Xu, S.; Li, Y. Org. Lett. 2021, 23, 757.
[5]
(g) Wei, W.; Scheremetjew, A.; Ackermann, L. Chem. Sci. 2022, 13, 2783.
[6]
For C—H spiroannulation reactions of phenols with alkynes in a racemic manner, see: (a) Seoane, A.; Casanova, N.; Quinones, N.; Mascaren?as, J. L.; Gulias, M. J. Am. Chem. Soc. 2014, 136, 7607.
[6]
(b) Kujawa, S.; Best, D.; Burns, D. J.; Lam, H. W. Chem. Eur. J. 2014, 20, 8599.
[6]
(c) Zuo, Z.; Yang, X.; Liu, J.; Nan, J.; Bai, L.; Wang, Y.; Luan, X. J. Org. Chem. 2015, 80, 3349.
[6]
(d) Lin, P.-P.; Han, X.-L.; Ye, G.-H.; Li, J.-L.; Li, Q.; Wang, H. J. Org. Chem. 2019, 84, 12966.
[6]
(e) Liu, A.; Han, K.; Wu, X.-X.; Chen, S.; Wang, J. Chin. J. Chem. 2020, 38, 1257.
[6]
(f) Liu, T.; Han, L.; Zhang, J.; Lu, G. J. Org. Chem. 2021, 86, 10484.
[7]
(a) Pettus, T. R. R.; Inoue, M.; Chen, X.-T.; Danishefsky, S. J. J. Am. Chem. Soc. 2000, 122, 6160.
[7]
(b) Zhan, Z.-J.; Li, C.-P.; Shan, W.-G. J. Chem. Res. 2007, 1, 38.
[7]
(c) Saito, Y.; Takashima, Y.; Kamada, A.; Suzuki, Y.; Suenaga, M.; Okamoto, Y.; Matsunaga, Y.; Hanai, R.; Kawahara, T.; Gong, X.; Tori, M.; Kuroda, C. Tetrahedron 2012, 68, 10011.
[7]
(d) Sandargo, B.; Michehl, M.; Praditya, D.; Steinmann, E.; Stadler, M.; Surup, F. Org. Lett. 2019, 21, 3286.
[8]
For selected reviews on Rh-catalyzed C—H functionalizations, see: (a) Ye, B.; Cramer, N. Acc. Chem. Res. 2015, 48, 1308.
[8]
(b) Yoshino, T.; Satake, S.; Matsunaga, S. Chem. Eur. J. 2020, 26, 7346.
[8]
(c) Shaaban, S.; Davies, C.; Waldmann, H. Eur. J. Org. Chem. 2020, 6512.
[8]
(d) Mas-Rosello, J.; Herraiz, A. G.; Audic, B.; Laverny, A.; Cramer, N. Angew. Chem., Int. Ed. 2021, 60, 13198.
[8]
(e) Davies, C.; Shaaban, S.; Waldmann, H. Trends Chem. 2022, 4, 318.
[9]
(a) Ye, B.; Cramer, N. Science 2012, 338, 504.
[9]
(b) Ye, B.; Cramer, N. J. Am. Chem. Soc. 2013, 135, 636.
[9]
(c) Zheng, J.; Cui, W.-J.; Zheng, C.; You, S.-L. J. Am. Chem. Soc. 2016, 138, 5242.
Options
文章导航

/

〈 〉