Highly stereoselective conjugate addition and α-alkynylation reaction with electron-deficient alkynes catalyzed by chiral scandium(III) complexes

Chemistry - A European Journal

Volumn 19, Issue 26, 2013, Pages 8591-8596

  Wang, Zhen ^a   Zhang, Zuliang ^a   Yao, Qian ^a   Liu, Xiaohua ^a   Cai, Yunfei ^a   Lin, Lili ^a   Feng, Xiaoming ^a  

^a China   (China)

Author keywords

acetylenic substitution; alkynes; N,N dioxides; oxindoles; scandium; Z selective

Indexed keywords

ALKYNES; ASYMMETRIC CONJUGATE ADDITION; CONJUGATE ADDITION; ELECTRON-DEFICIENT; GEOMETRIC CONTROL; OXINDOLES; STEREO-SELECTIVE; Z SELECTIVE;

CARBONYL COMPOUNDS; CATALYSTS; ENANTIOMERS; ENANTIOSELECTIVITY; HYDROCARBONS; SCANDIUM; SUBSTITUTION REACTIONS;

SCANDIUM COMPOUNDS;

EID: 84879187033     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201300816     Document Type: Article

References (70)

1. Acetylene Chemistry (Eds.:, F. Diederich, P. J. Stang, R. R. Tykwinski,), Wiley-VCH, Weinheim, 2005
2. R. C. Fahey, in Topics in Stereochemistry, Vol. 3 (Eds.:, N. L. Allinger, E. L. Eliel,), Wiley, New York, 2007, pp. 237-342.
3. J. W. Bode, E. M. Carreira, J. Am. Chem. Soc. 2001, 123, 3611
4. S. E. Denmark, S. M. Yang, J. Am. Chem. Soc. 2002, 124, 15196
5. G. Lalic, E. J. Corey, Org. Lett. 2007, 9, 4921
6. V. Hickmann, M. Alcarazo, A. Fürstner, J. Am. Chem. Soc. 2010, 132, 11042
7. T. L. May, J. A. Dabrowski, A. H. Hoveyda, J. Am. Chem. Soc. 2011, 133, 736.
8. M. Bella, K. A. Jørgensen, J. Am. Chem. Soc. 2004, 126, 5672
9. X. Wang, M. Kitamura, K. Maruoka, J. Am. Chem. Soc. 2007, 129, 1038
10. Q. Lan, X. Wang, K. Maruoka, Tetrahedron Lett. 2007, 48, 4675
11. Z. Chen, M. Furutachi, Y. Kato, S. Matsunaga, M. Shibasaki, Angew. Chem. 2009, 121, 2252
12. Angew. Chem. Int. Ed. 2009, 48, 2218
13. T. B. Poulsen, L. Bernardi, M. Bell, K. A. Jørgensen, Angew. Chem. 2006, 118, 6701
14. Angew. Chem. Int. Ed. 2006, 45, 6551. See also ref. [4-6].
15. C. Jia, W. Lu, J. Oyamada, T. Kitamura, K. Matsuda, M. Irie, Y. Fujiwara, J. Am. Chem. Soc. 2000, 122, 7252
16. R. B. Grossman, S. Comesse, R. M. Rasne, K. Hattori, M. N. Delong, J. Org. Chem. 2003, 68, 871
17. Z. Shi, C. He, J. Org. Chem. 2004, 69, 3669
18. A. J. Mueller, M. P. Jennings, Org. Lett. 2007, 9, 5327; for an exceptional E selectivity, see
19. A. Rubio, J. Ezquerra, Tetrahedron Lett. 1995, 36, 5823; see also ref. [21] for Z-selective conjugate addition.
20. T. Misaki, K. Kawano, T. Sugimura, J. Am. Chem. Soc. 2011, 133, 5695
21. Z. Wang, Z. L. Chen, S. Bai, W. Li, X. H. Liu, L. L. Lin, X. M. Feng, Angew. Chem. 2012, 124, 2830
22. Angew. Chem. Int. Ed. 2012, 51, 2776
23. D. Uraguchi, Y. Ueki, A. Sugiyama, T. Ooi, Chem. Sci. 2013, 4, 1308.
24. S. I. Miller, J. I. Dickstein, Acc. Chem. Res. 1976, 9, 358.
25. T. B. Poulsen, L. Bernardi, J. Alemán, J. Overgaard, K. A. Jørgensen, J. Am. Chem. Soc. 2007, 129, 441.
26. R. M. Williams, R. J. Cox, Acc. Chem. Res. 2003, 36, 127
27. A. B. Dounay, L. E. Overman, Chem. Rev. 2003, 103, 2945
28. H. Lin, S. J. Danishefsky, Angew. Chem. 2003, 115, 38
29. Angew. Chem. Int. Ed. 2003, 42, 36
30. C. Marti, E. M. Carreira, Eur. J. Org. Chem. 2003, 2209
31. C. V. Galliford, K. A. Scheidt, Angew. Chem. 2007, 119, 8902
32. Angew. Chem. Int. Ed. 2007, 46, 8748
33. B. M. Trost, M. K. Brennan, Synthesis 2009, 3003
34. F. Zhou, Y. L. Liu, J. Zhou, Adv. Synth. Catal. 2010, 352, 1381
35. K. Shen, X. H. Liu, L. L. Lin, X. M. Feng, Chem. Sci. 2012, 3, 327.
36. T. Bui, S. Syed, C. F. Barbas III, J. Am. Chem. Soc. 2009, 131, 8758
37. R. He, C. Ding, K. Maruoka, Angew. Chem. 2009, 121, 4629
38. Angew. Chem. Int. Ed. 2009, 48, 4559
39. Y. Kato, M. Furutachi, Z. Chen, H. Mitsunuma, S. Matsunaga, M. Shibasaki, J. Am. Chem. Soc. 2009, 131, 9168
40. R. He, S. Shirakawa, K. Maruoka, J. Am. Chem. Soc. 2009, 131, 16620
41. X. Li, B. Zhang, Z.-G. Xi, S. Luo, J.-P. Cheng, Adv. Synth. Catal. 2010, 352, 416
42. T. Zhang, L. Cheng, S. Hameed, L. Liu, D. Wang, Y.-J. Chen, Chem. Commun. 2011, 47, 6644
43. C. Wang, X. Yang, D. Enders, Chem. Eur. J. 2012, 18, 4832
44. F. R. Zhong, X. W. Dou, X. Y. Han, W. J. Yao, Q. Zhu, Y. Z. Meng, Y. X. Lu, Angew. Chem. 2013, 125, 977
45. Angew. Chem. Int. Ed. 2013, 52, 943.
46. During the preparation of this manuscript, an organocatalytic conjugate addition of N-Boc-oxindoles to butyl but-2-ynedioate was reported, see: G. W. Kang, Q. Q. Wu, M. C. Liu, Q. F. Xu, Z. Y. Chen, W. L. Chen, Y. Q. Luo, W. Ye, J. Jiang, H. Y. Wu, Adv. Synth. Catal. 2013, 355, 315.
47. J. Christoffers, A. Baro, Angew. Chem. 2003, 115, 1726
48. Angew. Chem. Int. Ed. 2003, 42, 1688
49. E. A. Peterson, L. E. Overman, Proc. Natl. Acad. Sci. USA 2004, 101, 11943
50. D. J. Ramon, M. Yus, Curr. Org. Chem. 2004, 8, 149
51. J. Christoffers, A. Baro, Adv. Synth. Catal. 2005, 347, 1473.
52. X. H. Liu, L. L. Lin, X. M. Feng, Acc. Chem. Res. 2011, 44, 574
53. X. M. Feng, X. H. Liu, in Scandium: Compounds, Productions and Applications (Ed.:, V. A. Greene,), Nova Science, New York, 2011, pp. 1-48
54. A. V. Malkov, P. Kočovský, Eur. J. Org. Chem. 2007, 29
55. G. Chelucci, G. Murineddu, G. A. Pinna, Tetrahedron: Asymmetry 2004, 15, 1373; for our work in this field, see
56. L. Zhou, X. H. Liu, J. Ji, Y. H. Zhang, X. L. Hu, L. L. Lin, X. M. Feng, J. Am. Chem. Soc. 2012, 134, 17023
57. W. Li, X. H. Liu, X. Y. Hao, Y. F. Cai, L. L. Lin, X. M. Feng, Angew. Chem. 2012, 124, 8772
58. Angew. Chem. Int. Ed. 2012, 51, 8644
59. K. Shen, X. H. Liu, G. Wang, L. L. Lin, X. M. Feng, Angew. Chem. 2011, 123, 4780
60. Angew. Chem. Int. Ed. 2011, 50, 4684.
61. J. K. Thomas, Chem. Rev. 1993, 93, 301
62. M. E. Davis, Acc. Chem. Res. 1993, 26, 111.
63. CCDC-921327 (N-Ts- 9 h) and CCDC-921328 (3 k) contains the supplementary crystallographic data of the adducts for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif
64. W. Steglich, P. Gruber, G. Höfle, W. König, Angew. Chem. 1971, 83, 725
65. Angew. Chem. Int. Ed. Engl. 1971, 10, 653
66. H. Wegmann, G. Schulz, W. Steglich, Liebigs Ann. Chem. 1980, 1736
67. A. Lõpez, M. Moreno-Mañas, R. Pleixats, A. Roglans, J. Ezquerra, C. Pedregal, Tetrahedron 1996, 52, 8365
68. G. Guillena, C. Nájera, J. Org. Chem. 2000, 65, 7310.
69. F. Freeman, D. S. H. L. Kim, J. Org. Chem. 1993, 58, 6474 and ref. [6].
70. For a leading reference on the protonation of allenic enols, see:, H. E. Zimmerman, A. Pushechnikov, Eur. J. Org. Chem. 2006, 3491.