Citation: Huo Yuwen, Shen Panpan, Duan Wenzeng, Chen Zhen, Song Chun, Ma Yudao. Metal-free catalytic enantioselective silylation of aromatic aldehydes in water[J]. Chinese Chemical Letters, ;2018, 29(9): 1359-1362. doi: 10.1016/j.cclet.2017.12.005 shu

Metal-free catalytic enantioselective silylation of aromatic aldehydes in water

Huo Yuwen ^a,1 ,
Shen Panpan ^a,1 ,
Duan Wenzeng ^b ,
Chen Zhen ^c ,
Song Chun ^a,, ,
Ma Yudao ^a,,

a.
Department of Chemistry, Shandong University, Jinan 250100, China
b.
School of Chemistry and Chemical Engineering, Liaocheng University, Liaocheng 252000, China
c.
School of Chemistry and Chemical Engineering, Hebei Normal University For Nationalities, Higher Education Park, Chengde 0670000, China

Corresponding author: Song Chun, chunsong@sdu.edu.cn Ma Yudao, ydma@sdu.edu.cn

Received Date: 24 October 2017
Revised Date: 21 November 2017
Accepted Date: 5 December 2017
Available Online: 6 September 2017

Figures(3)

An environmentally friendly and transition metal-free method for the preparation of chiral α-hydroxysilanes was developed. Enantioselective addition of a silicon nucleophile to aromatic aldehydes in water was achieved by using a new hydroxyl-functionalized chiral carbene as catalyst, affording the corresponding products in good yields and moderate enantioselectivities.
- Silylation,
- Asymmetric catalysis,
- N-Heterocyclic carbene,
- [2.2]Paracyclophane,
- αjjHydroxysilane
1. [1]
  T.H. Chan, D. Wang, Chem. Rev. 92(1992) 995-1006. doi: 10.1021/cr00013a012
2. [2]
  (a) T. Mita, M. Sugawara, K. Saito, Y. Sato, Org. Lett. 16(2014) 3028-3031;
  (b) K. Lee, A. H. Hoveyda, J. Am. Chem. Soc. 132(2010) 2898-2900;
  (c) M. Takeda, R. Shintani, T. Hayashi, J. Org. Chem. 78(2013) 5007-5017;
  (d) V. Pace, J. P. Rae, H. Y. Harb, D. J. Procter, Chem. Commun. 49(2013) 5150-5152;
  (e) C. Zhao, C. Jiang, J. Wang, Asian J. Org. Chem. 3(2014) 851-855;
  (f) M. Oestreich, E. Hartmann, M. Mewald, Chem. Rev. 113(2013) 402-441.
3. [3]
  (a) I. Fleming, A. Barbero, D. Walter, Chem. Rev. 97(1997) 2063-2192;
  (b) J. R. Huckins, S. D. Rychnovsky, J. Org. Chem. 68(2003) 10135-10145;
  (c) P. A. Jacobi, C. Tassa, Org. Lett. 5(2003) 4879-4882;
  (d) S. Perrone, P. Knochel, Org. Lett. 9(2007) 1041-1044.
4. [4]
  (a) K. Takeda, Y. Ohnishi, T. Koisumi, Org. Lett. 1(1999) 237-239;
  (b) N. Arai, K. Suzuki, S. Sugisaki, H. Sorimachi, T. Ohkuma, Angew. Chem. Int. Ed. 47(2008) 1770-1773;
  (c) J. I. Matsuo, Y. Hattori, H. Ishibashi, Org. Lett. 12(2010) 2294-2297;
  (d) P. A. Jacobi, C. Tassa, Org. Lett. 5(2003) 4879-4882.
5. [5]
  (a) L. Panella, B. L. Feringa, J. G. de Vries, A. J. Minnaard, Org. Lett. 7(2005) 4177-4180;
  (b) S. Bain, S. Ijadi-Maghsoodi, T. J. Barton, J. Am. Chem. Soc. 110(1988) 2611-2614.
6. [6]
  (a) P. C. Bulman, S. S. Klair, S. Rosenthal, Chem. Soc. Rev. 19(1990) 147-195;
  (b) R. B. Lettan Ⅱ, B. C. Milgram, K. A. Scheidt, Org. Synth. 84(2007) 22-31.
7. [7]
  C. Kleeberg, E. Feldmann, E. Hartmann, D.J. Vyas, M. Oestreich, Chem. Eur. J.17(2011) 13538-13543. doi: 10.1002/chem.v17.48
8. [8]
  V. Cirriez, C. Rasson, T. Hermant, et al., Angew. Chem. Int. Ed. 52(2013) 1785-1788. doi: 10.1002/anie.v52.6
9. [9]
  P. An, Y. Huo, Z. Chen, C. Song, Y. Ma, Org. Biomol. Chem.15(2017) 3202-3206. doi: 10.1039/C7OB00243B
10. [10]
  (a) T. Kitanosono, L. Zhu, C. Liu, P. Xu, S. Kobayashi, J. Am. Chem. Soc. 137(2015) 15422-15425;
  (b) S. Kobayashi, P. Xu, T. Endo, M. Ueno, T. Kitanosono, Angew. Chem. Int. Ed. 51(2012) 12763-12766.
11. [11]
  (a) M. O. Simon, C. J. Li, Chem. Soc. Rev. 41(2012) 1415-1427;
  (b) G. K. Min, D. Herna'ndez, T. Skrydstrup, Acc. Chem. Res. 46(2013) 457-470.
12. [12]
  (a) D. M. Flanigan, F. Romanov-Michailidis, N. A. White, T. Rovis, Chem. Rev. 115(2015) 9307-9387;
  (b) X. Wu, L. Hao, Y. Zhang, Angew. Chem. Int. Ed. 56(2017) 4201-4203;
  (c) X. Chen, K. Chen, D. Sun, S. Ye, Chem. Sci. 8(2017) 1936-1941;
  (d) K. Zhao, D. Enders, Angew. Chem. Int. Ed. 56(2017) 3754-3756;
  (e) G. Li, Q. Gu, S. You, Chem. Sci. 6(2015) 4273-4278;
  (f) J. Chen, P. Yuan, L. Wang, Y. Huang, J. Am. Chem. Soc. 139(2017) 7045-7051;
  (g) J. Xu, S. Zheng, J. Zhang, X. Liu, B. Tan, Angew. Chem. Int. Ed. 55(2016) 11834-11839;
  (h) G. Zhang, S. Yang, X. Zhang, et al., J. Am. Chem. Soc. 138(2016) 7932-7938;
  (i) J. Wu, C. Zhao, J. Wang, J. Am. Chem. Soc. 138(2016) 4706-4709.
13. [13]
  (a) X. L. Hou, X. W. Wu, L. X. Dai, B. X. Cao, J. Sun, Chem. Commun. (2000) 1195-1196;
  (b) X. W. Wu, X. L. Hou, L. X. Dai, Tetrahedron: Asymmetry 12(2001) 529-532;
  (c) B. Jiang, Y. Lei, X. Zhao, J. Org. Chem. 73(2008) 7833-7836;
  (d) L. Han, Y. Lei, X. Zhao, B. Jiang, J. Org. Chem. 80(2015) 3752-3757;
  (e) P. J. Pye, K. Rossen, R. A. Reamer, J. Am. Chem. Soc. 119(1997) 6207-6208;
  (f)C. Bolm, S. Dahmen, C. Bolm, S. Bräse, Angew. Chem. Int. Ed. 41(2002)3692-3694.
14. [14]
  Z. Chen, Y. Huo, P. An, et al., Org. Chem. Front. 3(2016) 1725-1737. doi: 10.1039/C6QO00386A
15. [15]
  (a) Y. Ma, S. Wei, J. Wu, et al., Adv. Synth. Catal. 350(2008) 2645-2651;
  (b) H. Lv, Y. Zhang, X. Huang, S. Ye, Adv. Synth. Catal. 350(2008) 2715-2718;
  (c) L. Zhao, Y. Ma, W. Duan, et al., Org. Lett. 14(2012) 5780-5783.
16. [16]
  (a) J. M. O'Brien, A. H. Hoveyda, J. Am. Chem. Soc. 133(2011) 7712-7715;
  (b) H. Wu, J. M. Garcia, F. Haeffner, et al., J. Am. Chem. Soc. 137(2015) 10585-10602.
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