Citation: Lin Tao, Zhao Qingyang, Zhang Xumu, Dong Xiu-Qin. Facile access to chiral 4-substituted chromanes through Rh-catalyzed asymmetric hydrogenation[J]. Chinese Chemical Letters, ;2020, 31(7): 1859-1862. doi: 10.1016/j.cclet.2020.01.001 shu

Facile access to chiral 4-substituted chromanes through Rh-catalyzed asymmetric hydrogenation

Lin Tao ^a ,
Zhao Qingyang ^b,c ,
Zhang Xumu ^a,b,*, ,
Dong Xiu-Qin ^a,*,

a.
Key Laboratory of Biomedical Polymers, Engineering Research Centre of Organosilicon Compounds & Materials, Ministry of Education, College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072, China
b.
Department of Chemistry and Shenzhen Grubbs Institute, Southern University of Science and Technology, Shenzhen 518055, China
c.
School of Pharmaceutical Sciences(Shenzhen), Sun Yat-sen University, Shenzhen 518107, China

^**

zhangxm@sustc.edu.cn

xiuqindong@whu.edu.cn

Received Date: 1 November 2019
Revised Date: 17 December 2019
Accepted Date: 2 January 2020
Available Online: 2 January 2020

Figures(6)

Rh/ZhaoPhos-catalyzed asymmetric hydrogenation of a series of (E)-2-(chroman-4-ylidene)acetates was successfully developed to prepare various chiral 4-substituted chromanes with high yields and excellent enantioselectivities (up to 99% yield, 98% ee). Moreover, the gram-scale hydrogenation could be performed well in the presence of 0.02 mol% catalyst loading (TON = 5000), the hydrogenation product was easily converted to access other important compounds, which demonstrated the synthetic utility of this asymmetric catalytic methodology.
- Chiral 4-substituted chromanes,
- Asymmetric hydrogenation,
- Excellent enantioselectivity,
- Gram-scale synthesis,
- Bisphosphine-thiourea ligand
1. [1]
  (a) G.R. Geen, J.M. Evans, A.K. Vong, Pyrans and their benzo derivatives: applications, in: A.R. Katritzky, C.W. Rees, E.F.V. Scriven (Eds.), Comprehensive Heterocyclic Chemistry Ⅱ, Vol. 5, PergamonPress, Oxford, UK, 1996, pp.469-500;
  (b) D.A. Horton, G.T. Boume, M.L. Smythe, Chem. Rev. 103 (2003) 893-930;
  (c) G.P. Ellis, Chromenes, chromanones, and chromones, in: A. Weissberger, E.C. Taylor (Eds.), The Chemistry of Heterocyclic Compounds, Vol. 31, Wiley-VCH, New York, 2007, pp. 1-1196;
  (d) K. Tatsuta, T. Tamura, T. Mase, Tetrahedron Lett. 40 (1999) 1925-1928;
  (e) Y. Kashiwada, K. Yamazaki, Y. Ikeshiro, et al., Tetrahedron 57 (2001) 1559-1563;
  (f) D.J. Maloney, J.Z. Deng, S.R. Starck, Z. Gao, S.M. Hecht, J. Am. Chem. Soc. 127 (2005) 4140-4141;
  (g) J.Z. Deng, S.R. Starck, S. Li, S.M. Hecht, J. Nat. Prod. 68 (2005) 1625-1628;
  (h) D.J. Maloney, S. Chen, S.M. Hecht, Org. Lett. 8 (2006) 1925-1927;
  (i) K.S. Choi, S.G. Kim, Tetrahedron Lett. 51 (2010) 5203-5206;
  (j) A.L. Lawrence, R.M. Adlington, E. Jack, et al., Org. Lett. 12 (2010) 1676-1679;
  (k) J.P. Lumb, J.L. Krinsky, D. Trauner, Org. Lett. 12 (2010) 5162-5365;
  (l) J.T.J. Spence, J.H. George, Org. Lett. 13 (2011) 5318-5321;
  (m) S.B. Bharate, R. Mudududdla, J.B. Bharate, et al., Org. Biomol. Chem. 10 (2012) 5143-5150;
  (n) J. Liu, X. Wang, L. Xu, et al., Tetrohedron 72 (2016) 7642-7649.
2. [2]
  (a) R. Ukis, C. Schneider, J. Org. Chem. 84 (2019) 7175-7188;
  (b) A.B. Xia, C. Wu, T. Wang, et al., Adv. Synth. Catal. 356 (2014) 1753-1760;
  (c) Z. Wu, S.D. Laffoon, K.L. Hull, Nat. Commun. 9 (2018) 1185-1192.
3. [3]
  (a) R. Maity, S.C. Pan, Org. Biomol. Chem. 16 (2018) 1598-1608;
  (b) Y. Lee, S.W. Seo, S.G. Kim, Adv. Synth. Catal. 353 (2011) 2671-2675;
  (c) K.S. Choi, S.G. Kim, Eur. J. Org. Chem. (2012) 1119-1122;
  (d) L. Zu, S. Zhang, H. Xie, W. Wang, Org. Lett. 11 (2009) 1627-1630.
4. [4]
  (a) D. Enders, C. Wang, X. Yang, G. Raabe, Adv. Synth. Catal. 352 (2010) 2869-2874;
  (b) D. Enders, X. Yang, C. Wang, G. Raabe, J. Runsik, Chem. -Asian J. 6 (2011) 2255-2259;
  (c) B.C. Hong, P. Kotame, J.H. Liao, Org. Biomol. Chem. 9 (2011) 382-386;
  (d) D.B. Ramachary, M.S. Prasad, R. Madhavachary, Org. Biomol. Chem. 9 (2011) 2715-2721;
  (e) S. Jakkampudi, R. Parella, J.C.G. Zhao, Org. Biomol. Chem. 17 (2019) 151-155;
  (f) D.B. Ramachary, R. Sakthidevi, K.S. Shruthi, Chem. -Eur. J. 18 (2012) 8008-8012;
  (g) D.B. Ramachary, P.S. Reddy, M.S. Prasad, Eur. J. Org. Chem. (2014) 3076-3081;
  (h) D. Lu, Y. Li, Y. Gong, J. Org. Chem. 75 (2010) 6900-6907;
  (i) J. Yang, G. Qiu, J. Jiang, et al., Adv. Synth. Catal. 359 (2017) 2184-2190.
5. [5]
  (a) Z. Wang, J. Sun, Org. Lett. 19 (2017) 2334-2337;
  (b) C.C. Hsiao, S. Raja, H.H. Liao, I. Atodiresei, M. Rueping, Angew. Chem. Int. Ed. 54 (2015) 5762-5765.
6. [6]
  (a) A. Song, X. Zhang, X. Song, et al., Angew. Chem. Int. Ed. 53 (2014) 4940-4944;
  (b) M. Spanka, C. Schneider, Org. Lett. 20 (2018) 4769-4772.
7. [7]
  G. Blay, M.C. Muñoz, J.R. Pedro, A.S. Marco, Adv. Synth. Catal. 355(2013) 1071-1076. doi: 10.1002/adsc.201201120
8. [8]
  D.A. Glazier, J.M. Schroeder, J. Liu, W. Tang, Adv. Synth. Catal. 360(2018) 4646-4649. doi: 10.1002/adsc.201800994
9. [9]
  W. Yang, Y. Liu, S. Zhang, Q. Cai, Angew. Chem. Int. Ed. 54(2015) 8805-8808. doi: 10.1002/anie.201503882
10. [10]
  R.M. Neyyappadath, D.B. Cordes, A.M.Z. Slawin, A.D. Smith, Chem. Commun. 53(2017) 2555-2558. doi: 10.1039/C6CC10178J
11. [11]
  Q.G. Wang, S.F. Zhu, L.W. Ye, et al., Adv. Synth. Catal. 352(2010) 1914-1919. doi: 10.1002/adsc.201000129
12. [12]
  K. Fukamizu, Y. Miyake, Y. Nishibayashi, J. Am. Chem. Soc. 130(2008) 10498-10499. doi: 10.1021/ja8038745
13. [13]
  (a) Y. Zhou, J.S. Bandar, R.Y. Liu, S.L. Buchwald, J. Am. Chem. Soc. 140 (2018) 606-609;
  (b) V. Hornillos, A.W. Zijl, B.L. Feringa, Chem. Commun. 48 (2012) 3712-3714;
  (c) R.C. Carmona, O.D. Köster, C.R.D. Correia, Angew. Chem. Int. Ed. 57 (2018) 12067-12070;
  (d) M. Wang, J. Chen, Z. Chen, C. Zhong, P. Lu, Angew. Chem. Int. Ed. 57 (2018) 2707-2711.
14. [14]
  (a) W.S. Knowles, Acc. Chem. Res. 16 (1983) 106-112;
  (b) R. Noyori, H. Takaya, Acc. Chem. Res. 23 (1990) 345-350;
  (c) R. Noyori, T. Ohkuma, Angew. Chem. Int. Ed. 40 (2001) 40-73;
  (d) W. Tang, X. Zhang, Chem. Rev. 103 (2003) 3029-3070;
  (e) H.U. Blaser, C. Malan, B. Pugin, et al., Adv. Synth. Catal. 345 (2003) 103-151;
  (f) X. Cui, K. Burgess, Chem. Rev. 105 (2005) 3272-3296;
  (g) A.J. Minnaard, B.L. Feringa, L. Lefort, J.G. De Vries, Acc. Chem. Res. 40 (2007) 1267-1277;
  (h) W. Zhang, Y. Chi, X. Zhang, Acc. Chem. Res. 40 (2007) 1278-1290;
  (i) N.B. Johnson, I.C. Lennon, P.H. Moran, J.A. Ramsden, Acc. Chem. Res. 40 (2007) 1291-1299;
  (j) Y.G. Zhou, Acc. Chem. Res. 40 (2007) 1357-1366;
  (k) S.J. Roseblade, A. Pfaltz, Acc. Chem. Res. 40 (2007) 1402-1411;
  (l) N. Fleury-Bregeot, V. de la Fuente, S. Castillón, C. Claver, ChemCatChem 2 (2010) 1346-1371;
  (m) J.H. Xie, S.F. Zhu, Q.L. Zhou, Chem. Rev. 111 (2011) 1713-1760;
  (n) D.S. Wang, Q.A. Chen, S.M. Lu, Y.G. Zhou, Chem. Rev. 112 (2012) 2557-2590;
  (o) J.H. Xie, S.F. Zhu, Q.L. Zhou, Chem. Soc. Rev. 41 (2012) 4126-4139;
  (p) Q.A. Chen, Z.S. Ye, Y. Duan, Y.G. Zhou, Chem. Soc. Rev. 42 (2013) 497-511;
  (q) J.J. Verendel, O. Pamies, M. Dieguez, P.G. Andersson, Chem. Rev. 114 (2014) 2130-2169;
  (r) Z. Zhang, N.A. Butt, W. Zhang, Chem. Rev. 116 (2016) 14769-14827.
15. [15]
  (a) J. Xia, Y. Nie, G. Yang, Y. Liu, W. Zhang, Org. Lett. 19 (2017) 4884-4887;
  (b) B. Qu, L.P. Samankumara, S. Ma, et al., Angew. Chem. Int. Ed. 53 (2014) 14428-14432.
16. [16]
  (a) S. Guo, J. (Steve) Zhou, Org. Lett. 18 (2016) 5344-5347;
  (b) S. Guo, P. Yang, J. (Steve) Zhou, Chem. Commun. 51 (2015) 12115-12117.
17. [17]
  (a) Q. Zhao, S. Li, K. Huang, R. Wang, X. Zhang, Org. Lett. 15 (2013) 4014-4017;
  (b) P. Li, M. Zhou, Q. Zhao, et al., Org. Lett. 18 (2016) 40-43;
  (c) Q. Zhao, J. Wen, R. Tan, et al., Angew. Chem. Int. Ed. 53 (2014) 8467-8470;
  (d) J. Wen, R. Tan, S. Liu, Q. Zhao, X. Zhang, Chem. Sci. 7 (2016) 3047-3051;
  (e) Z. Han, P. Li, Z. Zhang, et al., ACS Catal. 6 (2016) 6214-6218;
  (f) T. Zhang, J. Jiang, L. Yao, H. Geng, X. Zhang, Chem. Commun. 53 (2017) 9258-9261;
  (g) G. Liu, Z. Han, X.Q. Dong, X. Zhang, Org. Lett. 20 (2018) 5636-5639.
18. [18]
  (a) B.D. Gallagher, B.R. Taft, B.H. Lipshutz, Org. Lett. 11 (2009) 5374-5377;
  (b) F. Song, S. Lu, J. Gunnet, et al., J. Med. Chem. 50 (2007) 2807-2817.
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