Catalytic Aldol-Cyclization Cascade of 3-Isothiocyanato Oxindoles with α-Ketophosphonates for the Enantioselective Synthesis of β-Amino-α-hydroxyphosphonates

Organic Letters

Volumn 17, Issue 21, 2015, Pages 5508-5511

  Kayal, Satavisha ^a   Mukherjee, Santanu ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

3-HYDROXYBUTANAL; ALDEHYDE; INDOLE DERIVATIVE; ISOTHIOCYANIC ACID DERIVATIVE; OXINDOLE; PHOSPHONIC ACID DERIVATIVE; QUININE; SPIRO COMPOUND; THIOUREA;

CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

ALDEHYDES; CATALYSIS; CYCLIZATION; INDOLES; ISOTHIOCYANATES; MOLECULAR STRUCTURE; ORGANOPHOSPHONATES; QUININE; SPIRO COMPOUNDS; STEREOISOMERISM; THIOUREA;

EID: 84946763274     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/acs.orglett.5b02929     Document Type: Article

References (72)

1. Mucha, A.; Kafarski, P.; Berlicki, Ł. J. Med. Chem. 2011, 54, 5955 10.1021/jm200587f
2. Tao, M.; Bihovsky, R.; Wells, G. J.; Mallamo, J. P. J. Med. Chem. 1998, 41, 3912 10.1021/jm980325e
3. Patel, D. V.; Rielly-Gauvin, K.; Ryono, D. E.; Free, C. A.; Rogers, W. L.; Smith, S. A.; DeForrest, J. M.; Oehl, R. S.; Petrillo, E. W.; Jr. J. Med. Chem. 1995, 38, 4557 10.1021/jm00022a022
4. Wester, R. T.; Chambers, R. J.; Green, M. D.; Murphy, W. R. Bioorg. Med. Chem. Lett. 1994, 4, 2005 10.1016/S0960-894X(01)80553-9
5. Stowasser, B.; Budt, K.-H.; Jian-Qi, L.; Peyman, A.; Ruppert, D. Tetrahedron Lett. 1992, 33, 6625 10.1016/S0040-4039(00)61002-X
6. Patel, D. V.; Rielly-Gauvin, K.; Ryono, D. E. Tetrahedron Lett. 1990, 31, 5587 10.1016/S0040-4039(00)97903-6
7. Dellaria, J. F.; Jr.; Maki, R. G.; Stein, H. H.; Cohen, J.; Whittern, D.; Marsh, K.; Hoffman, D. J.; Plattner, J. J.; Perun, T. J. J. Med. Chem. 1990, 33, 534 10.1021/jm00164a011
8. Coeffard, V.; Beaudet, I.; Evain, M.; Le Grognec, E. L.; Quintard, J.-P. Eur. J. Org. Chem. 2008, 2008, 3344 10.1002/ejoc.200800208
9. Drag, M.; Pawelczak, M.; Kafarski, P. Chirality 2003, 15, S104 10.1002/chir.10261
10. Smith, A. B.; III; Yager, K. M.; Taylor, C. M. J. Am. Chem. Soc. 1995, 117, 10879 10.1021/ja00149a011
11. Allen, J. G.; Atherton, F. R.; Hall, M. J.; Hassall, C. H.; Holmes, S. W.; Lambert, R. W.; Nisbet, L. J.; Ringrose, P. S. Nature 1978, 272, 56 10.1038/272056a0
12. Dzięgielewski, M.; Pięta, J.; Kamińska, E.; Albrecht, Ł. Eur. J. Org. Chem. 2015, 677 10.1002/ejoc.201403184
13. Zhao, D.; Wang, R. Chem. Soc. Rev. 2012, 41, 2095 10.1039/C1CS15247E
14. Bhadury, P. S.; Li, H. Synlett 2012, 23, 1108 10.1055/s-0031-1290193
15. Albrecht, Ł.; Albrecht, A.; Krawczyk, H.; Jørgensen, K. A. Chem.-Eur. J. 2010, 16, 28 10.1002/chem.200902634
16. Ma, J.-A. Chem. Soc. Rev. 2006, 35, 630 10.1039/b517100h
17. Palacios, F.; Alonso, C.; de los Santos, J. M. Chem. Rev. 2005, 105, 899 10.1021/cr040672y
18. Zhou, F.; Liu, Y.-L.; Zhou, J. Adv. Synth. Catal. 2010, 352, 1381 10.1002/adsc.201000161
19. Galliford, C. V.; Scheidt, K. A. Angew. Chem.; Int. Ed. 2007, 46, 8748 10.1002/anie.200701342
20. Marti, C.; Carreira, E. M. Eur. J. Org. Chem. 2003, 2209 10.1002/ejoc.200300050
21. Lin, H.; Danishefsky, S. J. Angew. Chem.; Int. Ed. 2003, 42, 36 10.1002/anie.200390048
22. Cheng, D.; Ishihara, Y.; Tan, B.; Barbas, C. F.; III ACS Catal. 2014, 4, 743 10.1021/cs401172r
23. Hong, L.; Wang, R. Adv. Synth. Catal. 2013, 355, 1023 10.1002/adsc.201200808
24. Singh, G. S.; Desta, Z. Y. Chem. Rev. 2012, 112, 6104 10.1021/cr300135y
25. Ball-Jones, N. R.; Badillo, J. J.; Franz, A. K. Org. Biomol. Chem. 2012, 10, 5165 10.1039/c2ob25184a
26. Trost, B. M.; Brennan, M. K. Synthesis 2009, 3003 10.1055/s-0029-1216975
27. Tripathi, C. B.; Kayal, S.; Mukherjee, S. Org. Lett. 2012, 14, 3296 10.1021/ol3012666
28. Mastarz, P.; Kafarski, P. In Aminophosphonic and Aminophosphinic Acids-Chemistry and Biological Activity; Kukhar, V. P.; Hudson, H. R.; Eds.; John Wiley: Chichester, 2000; pp 1-31.
29. Wróblewski, A. E.; Piotrowska, D. G. Tetrahedron: Asymmetry 2000, 11, 2615 10.1016/S0957-4166(00)00203-2
30. Ojima, I.; Lin, S.; Wang, T. Curr. Med. Chem. 1999, 6, 927
31. Patel, D. V.; Rielly-Gauvin, K.; Ryono, D. E. Tetrahedron Lett. 1990, 31, 5591 10.1016/S0040-4039(00)97904-8
32. Seo, Y. J.; Kim, J.; Lee, H.-K. J. Org. Chem. 2015, 80, 8887 10.1021/acs.joc.5b01434
33. Zhang, H.; Wen, X.; Gan, L.; Peng, Y. Org. Lett. 2012, 14, 2126 10.1021/ol300664d
34. Cao, Y.-M.; Shen, F.-F.; Zhang, F.-T.; Zhang, J.-L.; Wang, R. Angew. Chem.; Int. Ed. 2014, 53, 1862 10.1002/anie.201308514
35. Han, W.-Y.; Zhao, J.-Q.; Wu, Z.-J.; Zhang, X.-M.; Yuan, W.-C. J. Org. Chem. 2013, 78, 10541 10.1021/jo401779x
36. Togni, A.; Pastor, S. D. Tetrahedron Lett. 1989, 30, 1071 10.1016/S0040-4039(01)80362-2
37. Cravotto, G.; Giovenzana, G. B.; Pagliarin, R.; Palmisano, G.; Sisti, M. Tetrahedron: Asymmetry 1998, 9, 745 10.1016/S0957-4166(98)00038-X
38. Thomas, A. A.; Sharpless, K. B. J. Org. Chem. 1999, 64, 8379 10.1021/jo990060r
39. Mandal, T.; Samanta, S.; Zhao, C.-G. Org. Lett. 2007, 9, 943 10.1021/ol070209i
40. Chen, X.; Wang, J.; Zhu, Y.; Shang, D.; Gao, B.; Liu, X.; Feng, X.; Su, Z.; Hu, C. Chem.-Eur. J. 2008, 14, 10896 10.1002/chem.200801958
41. Serrano, I.; Monge, D.; álvarez, E.; Fernández, R.; Lassaletta, J. M. Chem. Commun. 2015, 51, 4077 10.1039/C4CC10390D
42. Kumar, A.; Sharma, V.; Kaur, J.; Kumar, V.; Mahajan, S.; Kumar, N.; Chimni, S. S. Tetrahedron 2014, 70, 7044 10.1016/j.tet.2014.06.013
43. George, J.; Sridhar, B.; Reddy, B. V. S. Org. Biomol. Chem. 2014, 12, 1595 10.1039/c3ob42026d
44. Zhao, J.-Q.; Zhou, M.-Q.; Wu, Z.-J.; Wang, Z.-H.; Yue, D.-F.; Xu, X.-Y.; Zhang, X.-M.; Yuan, W.-C. Org. Lett. 2015, 17, 2238 10.1021/acs.orglett.5b00850
45. Cai, H.; Zhou, Y.; Zhang, D.; Xu, J.; Liu, H. Chem. Commun. 2014, 50, 14771 10.1039/C4CC06000H
46. Kayal, S.; Mukherjee, S. Eur. J. Org. Chem. 2014, 6696 10.1002/ejoc.201402534
47. Tan, F.; Lu, L.-Q.; Yang, Q.-Q.; Guo, W.; Bian, Q.; Chen, J.-R.; Xiao, W.-J. Chem.-Eur. J. 2014, 20, 3415 10.1002/chem.201303583
48. Liu, X.-L.; Han, W.-Y.; Zhang, X.-M.; Yuan, W.-C. Org. Lett. 2013, 15, 1246 10.1021/ol400183k
49. Chen, Q.; Liang, J.; Wang, S.; Wang, D.; Wang, R. Chem. Commun. 2013, 49, 1657 10.1039/c3cc38386e
50. Jiang, Y.; Pei, C.-K.; Du, D.; Li, X.-G.; He, Y.-N.; Xu, Q.; Shi, M. Eur. J. Org. Chem. 2013, 7895 10.1002/ejoc.201301418
51. Han, W.-Y.; Li, S.-W.; Wu, Z.-J.; Zhang, X.-M.; Yuan, W.-C. Chem.-Eur. J. 2013, 19, 5551 10.1002/chem.201300206
52. Tan, F.; Cheng, H.-G.; Feng, B.; Zou, Y.-Q.; Duan, S.-W.; Chen, J.-R.; Xiao, W.-J. Eur. J. Org. Chem. 2013, 2013, 2071 10.1002/ejoc.201300081
53. Kato, S.; Kanai, M.; Matsunaga, S. Chem.-Asian J. 2013, 8, 1768 10.1002/asia.201300251
54. Wu, H.; Zhang, L.-L.; Tian, Z.-Q.; Huang, Y.-D.; Wang, Y.-M. Chem.-Eur. J. 2013, 19, 1747 10.1002/chem.201203221
55. Cao, Y.-M.; Shen, F.-F.; Zhang, F.-T.; Wang, R. Chem.-Eur. J. 2013, 19, 1184 10.1002/chem.201204114
56. Kato, S.; Yoshino, T.; Shibasaki, M.; Kanai, M.; Matsunaga, S. Angew. Chem.; Int. Ed. 2012, 51, 7007 10.1002/anie.201203005
57. Chen, W.-B.; Wu, Z.-J.; Hu, J.; Cun, L.-F.; Zhang, X.-M.; Yuan, W.-C. Org. Lett. 2011, 13, 2472 10.1021/ol200724q
58. For a review, see: Han, W.-Y.; Zhao, J.-Q.; Zuo, J.; Xu, X.-Y.; Zhang, X.-M.; Yuan, W.-C. Adv. Synth. Catal. 2015, 357, 3007 10.1002/adsc.201500264
59. Bernardi, L.; Fini, F.; Herrera, R. P.; Ricci, A.; Sgarzani, V. Tetrahedron 2006, 62, 375 10.1016/j.tet.2005.09.076
60. McCooey, S. H.; Connon, S. J. Angew. Chem.; Int. Ed. 2005, 44, 6367 10.1002/anie.200501721
61. Ye, J.; Dixon, D. J.; Hynes, P. S. Chem. Commun. 2005, 4481 10.1039/b508833j
62. Vakulya, B.; Varga, S.; Csámpai, A.; Soós, T. Org. Lett. 2005, 7, 1967 10.1021/ol050431s
63. Li, B.-J.; Jiang, L.; Liu, M.; Chen, Y.-C.; Ding, L.-S.; Wu, Y. Synlett 2005, 603 10.1055/s-2005-863710
64. Okino, T.; Hoashi, Y.; Takemoto, Y. J. Am. Chem. Soc. 2003, 125, 12672 10.1021/ja036972z
65. Siau, W.-Y.; Wang, J. Catal. Sci. Technol. 2011, 1, 1298 10.1039/c1cy00271f
66. Connon, S. J. Chem. Commun. 2008, 2499 10.1039/b719249e
67. CCDC 1429374 contains the crystallographic data for 3af. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data
68. Choudhury, A. R.; Mukherjee, S. Org. Biomol. Chem. 2012, 10, 7313 10.1039/c2ob25832c
69. Wynberg, H.; Staring, E. G. J. J. Am. Chem. Soc. 1982, 104, 166 10.1021/ja00365a030
70. Kang, T.-H.; Matsumoto, K.; Tohda, M.; Murakami, Y.; Takayama, H.; Kitajima, M.; Aimi, N.; Watanabe, H. Eur. J. Pharmacol. 2002, 444, 39 10.1016/S0014-2999(02)01608-4
71. Pedras, M. S. C.; Okanga, F. I.; Zaharia, I. L.; Khan, A. Q. Phytochemistry 2000, 53, 161 10.1016/S0031-9422(99)00494-X
72. Baur, E.; Stadler, K.; Monde, K.; Takasugi, M. Chemoecology 1998, 8, 163 10.1007/s000490050021