Citation: Xiaohan Chen, Ran Zhao, Ziqiang Liu, Shutao Sun, Yingang Ma, Qingyun Liu, Xia Sun, Lei Liu. Redox deracemization of α-substituted 1, 3-dihydroisobenzofurans[J]. Chinese Chemical Letters, ;2021, 32(7): 2305-2308. doi: 10.1016/j.cclet.2021.02.021 shu

Redox deracemization of α-substituted 1, 3-dihydroisobenzofurans

Xiaohan Chen ^{a, b, 1} ,
Ran Zhao ^{a, 1} ,
Ziqiang Liu ^{a, e} ,
Shutao Sun ^c ,
Yingang Ma ^a ,
Qingyun Liu ^{b, **,} ,
Xia Sun ^{e, **,} ,
Lei Liu ^{a, c, d, *,}

a.
School of Pharmaceutical Sciences, Cheeloo College of Medicine, Shandong University, Ji'nan 250012, China
b.
College of Chemical and Biological Engineering, State Key Laboratory of Mining Disaster Prevention and Control Co-founded by Shandong Province and the Ministry of Science and Technology, Shandong University of Science and Technology, Qingdao 266590, China
c.
School of Chemistry and Chemical Engineering, Shandong University, Ji'nan 250100, China
d.
Shenzhen Research Institute of Shandong University, Shenzhen 518057, China
e.
Department of Pharmacology, School of Basic Medical Sciences, Cheeloo College of Medicine, Shandong University, Ji'nan 250012, China

^**

qyliu@sdust.edu.cn

sunxia@sdu.edu.cn

leiliu@sdu.edu.cn

Received Date: 8 December 2020
Revised Date: 4 February 2021
Accepted Date: 9 February 2021
Available Online: 16 February 2021

Figures(5)

Chiral α-substituted 1, 3-dihydroisobenzofurans are key scaffolds in a number of bioactive natural products and synthetic pharmaceuticals. However, catalytic asymmetric approaches have been rarely developed. Here, a redox deracemization technology is adopted to address the catalytic asymmetric synthesis. A broad range of α-aryl substituted 1, 3-dihydroisobenzofurans are effectively deracemized in high efficiency with excellent ee. α-Alkynyl substituted ethers were also compatible with the deracemization technology.
- 1, 3-Dihydroisobenzofuran,
- Asymmetric catalysis,
- Redox deracemization,
- Oxocarbenium ion,
- Synthetic method
1. [1]
  (a) V.J. Bauer, B.J. Duffy, D. Hoffman, et al., J. Med. Chem. 19 (1976) 1315-1324;
  (b) E.G. Maestrup, C. Wiese, D. Schepmann, et al., Bioorg. Med. Chem. 19 (2011) 393-405.
2. [2]
  (a) I. Čorić, J.H. Kim, T. Vlaar, et al., Angew. Chem. Int. Ed. 52 (2013) 3490-3493;
  (b) B. Ravindra, B.G. Das, P. Ghorai, Org. Lett. 16 (2014) 5580-5583;
  (c) D. Chen, S.R. Chemler, Org. Lett. 20 (2018) 6453-6456;
  (d) D. Chen, I.A. Berhane, S.R. Chemler, Org. Lett. 22 (2020) 7409-7414.
3. [3]
  N.M. Weldy, A.G. Schafer, C.P. Owens, et al., Chem. Sci. 7 (2016) 3142-3146. doi: 10.1039/C6SC00190D
4. [4]
  (a) S. Sun, Y. Ma, Z. Liu, L. Liu, Angew. Chem. Int. Ed. 60 (2021) 176-180;
  (b) S. Sun, Y. Yang, R. Zhao, D. Zhang, L. Liu, J. Am. Chem. Soc. 142 (2020) 19346-19353.
5. [5]
  (a) K. Faber, Chem. Eur. J. 7 (2001) 5004-5010;
  (b) C.C. Gruber, I. Lavandera, K. Faber, W. Kroutil, Adv. Synth. Catal. 348 (2006) 1789-1805;
  (c) N.J. Turner, Curr. Opin. Chem. Biol. 14 (2010) 115-121;
  (d) M. Rachwalski, N. Vermue, F.P.J.T. Rutjes, Chem. Soc. Rev. 42 (2013) 9268-9282;
  (e) R.C. Simon, N. Richter, E. Busto, W. Kroutil, ACS Catal. 4 (2014) 129-143.
6. [6]
  (a) A. Hölzl-Hobmeier, A. Bauer, A.V. Silva, et al., Nature 564 (2018) 240-243;
  (b) A. Tröster, A. Bauer, C. Jandl, T. Bach, Angew. Chem. Int. Ed. 58 (2019) 3538-3541;
  (c) N.Y. Shin, J.M. Ryss, X. Zhang, et al., Science 366 (2019) 364-369.
7. [7]
  (a) C.V. Voss, C.C. Gruber, W. Kroutil, Angew. Chem. Int. Ed. 47 (2008) 741-745;
  (b) C.V. Voss, C.C. Gruber, K. Faber, et al., J. Am. Chem. Soc. 130 (2008) 13969-13972;
  (c) C.J. Dunsmore, R. Carr, T. Fleming, et al., J. Am. Chem. Soc. 128 (2006) 2224-2225;
  (d) D. Ghislieri, A.P. Green, M. Pontini, et al., J. Am. Chem. Soc. 135 (2013) 10863-10869;
  (e) K. Yasukawa, S. Nakano, Y. Asano, Angew. Chem. Int. Ed. 53 (2014) 4428-4431.
8. [8]
  (a) Y. Shimada, Y. Miyake, H. Matsuzawa, et al., Chem. Asian J. 2 (2007) 393-396;
  (b) G.R.A. Adair, J.M.J. Williams, Chem. Commun (2007) 2608-2609;
  (c) P. Qu, M. Kuepfert, S. Jockusch, et al., ACS Catal. 9 (2019) 2701-2706;
  (d) A.D. Lackner, A.V. Samant, F.D. Toste, J. Am. Chem. Soc. 135 (2013) 14090-14093;
  (e) Y. Ji, L. Shi, M.W. Chen, et al., J. Am. Chem. Soc. 137 (2015) 10496-10499;
  (f) L. Zhang, R. Zhu, A. Feng, et al., Chem. Sci. 11 (2020) 4444-4449.
9. [9]
  (a) Y. Mao, Z. Wang, G. Wang, et al., ACS Catal. 10 (2020) 7785-7791;
  (b) Y. Ma, X. Liu, Y. Mao, et al., Org. Chem. Front. 7 (2020) 2526-2530.
10. [10]
  M. Wan, S. Sun, Y. Li, et al., Angew. Chem. Int. Ed. 56 (2017) 5116-5120. doi: 10.1002/anie.201701439
11. [11]
  (a) T. Akiyama, Chem. Rev. 107 (2007) 5744-5758;
  (b) M. Terada, Synthesis 42 (2010) 1929-1982;
  (c) D. Parmar, E. Sugiono, S. Raja, et al., Chem. Rev. 114 (2014) 9047-9153;
  (d) I. Cori Čorić, B. List, Nature 483 (2012) 315-319;
  (e) C. Zheng, S.L. You, Chem. Soc. Rev. 41 (2012) 2498-2518;
  (f) D. Wang, D. Astruc, Chem. Rev. 115 (2015) 6621-6686.
12. [12]
  (a) R. Zhao, G. Feng, X. Xin, et al., Chin. Chem. Lett. 30 (2019) 1432-1434;
  (b) Z. Wang, Y. Mao, H. Guan, et al., Chin. Chem. Lett. 30 (2019) 1241-1243;
  (c) P. Ye, X. Liu, G. Wang, L. Liu, Chin. Chem. Lett. 32 (2021) 1237-1240;
  (d) H. Guan, L. Chen, L. Liu, Acta Chim. Sinica 76 (2018) 440-444.
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