Citation: Pogula Sreekanth Reddy, Motakatla Venkata Krishna Reddy, Peddiahgari Vasu Govardhana Reddy. Camphor-derived thioureas: Synthesis and application in asymmetric Kabachnik-Fields reaction[J]. Chinese Chemical Letters, ;2016, 27(6): 943-947. doi: 10.1016/j.cclet.2016.01.046 shu

Camphor-derived thioureas: Synthesis and application in asymmetric Kabachnik-Fields reaction

Department of Chemistry, Yogi Vemana University, Kadapa 516003, Andhra Pradesh, India

Received Date: 2 November 2015
Revised Date: 29 December 2015

Fund Project: This project was supported by the Department of Science and Technology (DST), New Delhi, India (No. SR/FT/CS-013/2010) and is gratefully acknowledged.

A series of camphor-derived thiourea organocatalysts 3a-f were designed and synthesized from (1R,3S)-camphoric acid 1 and applied to the one-pot three-component Kabachnik-Fields reaction. Catalyst 3c was found to be an efficient organocatalyst for the reaction of 2-cyclopropylpyrimidin-4-carbaldehyde 4, various amines 5, and diphenylphosphite 6 to yield the corresponding enantioselective a-aminophosphonates 7a-e in 74%-82% yields and 14%-35% ee.
- Asymmetric organocatalysis,
- (1R,3S)-Camphoric acid,
- Camphor-derived thioureas,
- Chiral a-aminophosphonates,
- Enantioselective Kabachnik-Fields reaction
1. [1]
2. [2]
3. [3]
4. [4]
5. [5]
6. [6]
7. [7]
8. [8]
9. [9]
10. [10]
11. [11]
12. [12]
13. [13]
14. [14]
15. [15]
16. [16]
17. [17]
18. [18]
19. [19]
20. [20]
21. [21]
22. [22]
23. [23]
24. [24]
25. [25]
26. [26]
27. [27]
28. [28]
29. [29]
30. [30]
31. [31]
32. [32]
33. [33]
34. [34]
35. [35]
36. [36]
37. [37]
38. [38]
39. [39]
40. [40]
41. [41]
42. [42]
43. [43]
44. [44]
45. [45]
46. [46]
47. [47]
48. [48]
49. [49]
50. [50]
51. [51]
52. [52]
53. [53]
54. [54]
1. [1]
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2. [2]
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8. [8]
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9. [9]
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沈阳化工大学材料科学与工程学院沈阳 110142