Atom- and step-economical preparation of reduced knoevenagel adducts using CO as a deoxygenative agent

Organic Letters

Volumn 16, Issue 19, 2014, Pages 5068-5071

  Kolesnikov, Pavel N ^a   Usanov, Dmitry L ^a,b   Barablina, Evgeniya A ^a   Maleev, Victor I ^a   Chusov, Denis ^a  

^a A N NESMEYANOV INSTITUTE OF ORGANOELEMENT COMPOUNDS   (Russian Federation)

^b HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84907702012     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol502424t     Document Type: Article

References (76)

1. Trost, B. M. Science 1991, 254, 1471-1477
2. Wender, P. A.; Croatt, M. P.; Witulski, B. Tetrahedron 2006, 62, 7505-7511
3. Wender, P. A.; Verma, V. A.; Paxton, T. J.; Pillow, T. H. Acc. Chem. Res. 2008, 41, 40-49
4. Wender, P. A. Tetrahedron 2013, 69, 7529-7550
5. Richter, J. M.; Ishihara, Y.; Masuda, T.; Whitefield, B. W.; Llamas, T.; Pohjakallio, A.; Baran, P. S. J. Am. Chem. Soc. 2008, 130, 17938-17954
6. Burns, N. Z.; Baran, P. S.; Hoffmann, R. W. Angew. Chem., Int. Ed. 2009, 48, 2854-2867
7. Newhouse, T.; Baran, P. S.; Hoffmann, R. W. Chem. Soc. Rev. 2009, 38, 3010-3021
8. Trost, B. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 259-281
9. Trost, B. M. Acc. Chem. Res. 2002, 35, 695-705
10. Trost, B. M.; Frederiksen, M. U.; Rudd, M. T. Angew. Chem., Int. Ed. 2005, 44, 6630-6666
11. Iida, H.; Krische, M. J. Top. Curr. Chem. 2007, 279, 77-104
12. Fustero, S.; Sánchez-Roselló, M.; del Pozo, C. Pure Appl. Chem. 2010, 82, 669-677
13. Trost, B. M.; Brindle, C. S. Chem. Soc. Rev. 2010, 39, 1600-1632
14. Kumagai, N. Chem. Pharm. Bull. 2011, 59, 1-22
15. Hilt, G. Eur. J. Org. Chem. 2012, 4441-4451
16. Marson, C. M. Chem. Soc. Rev. 2012, 41, 7712-7722
17. Kotha, S.; Goyal, D.; Chavan, A. S. J. Org. Chem. 2013, 78, 12288-12313
18. Sebren, L. J.; Devery, J. J.; Stephenson, C. R. J. ACS Catal. 2013, 4, 703-716
19. Peng, B.; Maulide, N. Chem. - Eur. J. 2013, 19, 13274-13287
20. Xie, J.; Jin, H.; Xu, P.; Zhu, C. Tetrahedron Lett. 2014, 55, 36-48
21. Sohn, S. S.; Bode, J. W. Org. Lett. 2005, 7, 3873-3876
22. Löfberg, C.; Grigg, R.; Whittaker, M. A.; Keep, A.; Derrick, A. J. Org. Chem. 2006, 71, 8023-8027
23. Zeitler, K. Org. Lett. 2006, 8, 637-640
24. Haak, E. Eur. J. Org. Chem. 2008, 5, 788-792
25. Trost, B. M.; Livingston, R. C. J. Am. Chem. Soc. 2008, 130, 11970-11978
26. Trost, B. M.; Maulide, N.; Livingston, R. C. J. Am. Chem. Soc. 2008, 130, 16502-16503
27. Zeitler, K.; Rose, C. A. J. Org. Chem. 2009, 74, 1759-1762
28. Trost, B. M.; Gutierrez, A. C.; Livingston, R. C. Org. Lett. 2009, 11, 2539-2542
29. Goto, A.; Naka, H.; Noyori, R.; Saito, S. Chem. - Asian. J. 2011, 6, 1740-1743
30. Lumbroso, A.; Koschker, P.; Vautravers, N. R.; Breit, B. J. Am. Chem. Soc. 2011, 133, 2386-2389
31. Trost, B. M.; Breder, A.; O'Keefe, B. M.; Rao, M.; Franz, A. W. J. Am. Chem. Soc. 2011, 133, 4766-4769
32. Trost, B. M.; Breder, A. Org. Lett. 2011, 13, 398-401
33. Trost, B. M.; Lumb, J.-P.; Azzarelli, J. M. J. Am. Chem. Soc. 2011, 133, 740-743
34. Jonek, A.; Berger, S.; Haak, E. Chem. - Eur. J. 2012, 18, 15504-15511
35. Li, Y.; Zhang, X.-S.; Chen, K.; He, K.-H.; Pan, F.; Li, B.-J.; Shi, Z.-J. Org. Lett. 2012, 14, 636-639
36. Lumbroso, A.; Abermil, N.; Breit, B. Chem. Sci. 2012, 3, 789-793
37. Nguyen, T. B.; Ermolenko, L.; Al-Mourabit, A. J. Am. Chem. Soc. 2012, 135, 118-121
38. Thies, N.; Hrib, C. G.; Haak, E. Chem. - Eur. J. 2012, 18, 6302-6308
39. Trost, B. M.; Breder, A.; Kai, B. Org. Lett. 2012, 14, 1708-1711
40. Kang, B.; Fu, Z.; Hong, S. H. J. Am. Chem. Soc. 2013, 135, 11704-11707
41. Nguyen, T. B.; Ermolenko, L.; Al-Mourabit, A. Org. Lett. 2013, 15, 4218-4221
42. Nguyen, T. B.; Retailleau, P.; Al-Mourabit, A. Org. Lett. 2013, 15, 5238-5241
43. Thies, N.; Gerlach, M.; Haak, E. Eur. J. Org. Chem. 2013, 32, 7354-7365
44. Muralirajan, K.; Cheng, C.-H. Adv. Synth. Catal. 2014, 356, 1571-1576
45. Nakai, K.; Yoshida, Y.; Kurahashi, T.; Matsubara, S. J. Am. Chem. Soc. 2014, 136, 7797-7800
46. Roudier, M.; Constantieux, T.; Quintard, A.; Rodriguez, J. Org. Lett. 2014, 16, 2802-2805
47. Talbot, E. P. A.; Richardson, M.; McKenna, J. M.; Toste, F. D. Adv. Synth. Catal. 2014, 356, 687-691
48. Peng, B.; Huang, X.; Xie, L.-G.; Maulide, N. Angew. Chem., Int. Ed. 2014, 53, 8718-8721
49. Yürüm, Y. Hydrogen Energy System; Kluwer Academic Publishers: Dordrecht, Netherlands, 1994; p 16.
50. Romm, J. J. The Hype about Hydrogen; Island Press: Washington, DC, 2004; p 72.
51. Sheldon, R. A. Chem. Soc. Rev. 2012, 41, 1437-1451
52. Tietze, L. F.; Beifuss, U. In Comprehensive Organic Synthesis, Vol. 2; Trost, B. M.; Fleming, I., Eds.; Pergamon Press, Oxford, 1991; p 341.
53. Ebitani, K. In Comprehensive Organic Synthesis II, Vol. 2; Knochel, P.; Molander, G. A., Eds.; Amsterdam, 2014; p 571.
54. Couladouros, E. A.; Pitsinos, E. N.; Moutsos, V. I.; Sarakinos, G. Chem. - Eur. J. 2005, 11, 406-421
55. Coleman, R. S.; Campbell, E. L.; Carper, D. J. Org. Lett. 2009, 11, 2133-2136
56. Hong, S.; Lee, M.; Jung, M.; Park, Y.; Kim, M.-H.; Park, H.-G. Tetrahedron Lett. 2012, 53, 4209-4211
57. Debarge, S.; McDaid, P.; O'Neill, P.; Frahill, J.; Wong, J. W.; Carr, D.; Burell, A.; Davies, S.; Karmilowicz, M.; Steflik, J. Org. Process Res. Dev. 2014, 18, 109-121
58. Madivada, L. R.; Anumala, R. R.; Gilla, G.; Alla, S.; Charagondla, K.; Kagga, M.; Bhattacharya, A.; Bandichhor, R. Org. Process Res. Dev. 2009, 13, 1190-1194
59. Ramachary, D. B.; Kishor, M.; Reddy, Y. V. Eur. J. Org. Chem. 2008, 975-993
60. Ramachary, D. B.; Venkaiah, C.; Reddy, Y. V. Org. Biomol. Chem. 2014, 12, 5400-5406
61. Ramachary, D. B.; Kishor, M. Org. Biomol. Chem. 2010, 8, 2859-2867
62. Chusov, D.; List, B. Angew. Chem., Int. Ed. 2014, 53, 5199-5201
63. Bhardwaj, B. P. Steel and Iron Handbook; NPCS: Delhi, 2014.
64. Cheung, H.; Tanke, R. S.; Torrence, G. P. Acetic Acid, Ullmann's Encyclopedia of Industrial Chemistry; Wiley-VCH: 2005.
65. Ragaini, F.; Cenini, S.; Gallo, E.; Caselli, A.; Fantauzzi, S. Curr. Org. Chem. 2006, 10, 1479-1510
66. Wu, X.-F.; Neumann, H.; Beller, M. Angew. Chem., Int. Ed. 2010, 49, 5284-5288
67. Klein, H.; Jackstell, R.; Netscher, T.; Bonrath, W.; Beller, M. ChemCatChem 2011, 3, 1273-1276
68. Fang, X.; Jackstell, R.; Beller, M. Angew. Chem., Int. Ed. 2013, 52, 14089-14093
69. Wu, X.-F; Neumann, H.; Beller, M. ChemSusChem 2013, 6, 229-241
70. Fleischer, I.; Wu, L.; Profir, I.; Jackstell, R.; Franke, R.; Beller, M. Chem. - Eur. J. 2013, 19, 10589-10594
71. Schranck, J.; Wu, X.-F; Tlili, A.; Neumann, H.; Beller, M. Chem. - Eur. J. 2013, 19, 12959-12964
72. Pospech, J.; Fleischer, I.; Franke, R.; Buchholz, S.; Beller, M. Angew. Chem., Int. Ed. 2013, 52, 2852-2872
73. Pfizer Inc.; 2013, Financial Report.
74. Roy, B. N.; Singh, G. P.; Lathi, P.; Agrawal, M.; Mitra, R.; Rupnawar, M. D. Process for Synthesis of (S)-Pregabalin. WO2012059797, 2012.
75. Burell, A. J. M; Martinez, C. A.; McDaid, P. O.; O'Neill, P. M.; Wong, J. W. Process for the Preparation of (S)-3-Cyano-5-Methylhexanoic Acid Derivatives Adn of Pregabalin, WO2012025861, 2012.
76. Harada, H.; Iizuka, K.; Kamijo, T.; Akahane, K.; Yamamoto, R.; Nakano, Y.; Tsubaki, A.; Kubota, T.; Shimaoka, I.; Umeyama, H.; Kiso, Y. Chem. Pharm. Bull. 1990, 38, 3042-3047