A Csp3-Csp3 bond forming reductive condensation of α-keto esters and enolizable carbon pronucleophiles

Organic Letters

Volumn 15, Issue 12, 2013, Pages 3090-3093

  Zhao, Wei ^a   Fink, Darla M ^a   Labutta, Carolyn A ^a   Radosevich, Alexander T ^a  

^a PENNSYLVANIA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; DIMETHYLAMINE; ESTER; KETONE; PHOSPHINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY;

CARBON; CATALYSIS; DIMETHYLAMINES; ESTERS; KETONES; MOLECULAR STRUCTURE; PHOSPHINES;

EID: 84879396793     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol401276b     Document Type: Article

References (79)

1. Paal, C. Ber. Dtsch. Chem. Ges. 1884, 17, 2756
2. Knorr, L. Ber. Dtsch. Chem. Ges. 1884, 17, 2863
3. For instance, see: Whittaker, M.; Floyd, C. D.; Brown, P.; Gearing, A. J. H. Chem. Rev. 1999, 99, 2735
4. Stetter, H.; Kuhlmann, H. Org. React. 1991, 40, 407
5. Enders, D.; Breuer, K.; Runsink, J.; Teles, J. H. Helv. Chim. Acta 1996, 79, 1899
6. Kerr, M. S.; Read de Alaniz, J.; Rovis, T. J. Am. Chem. Soc. 2002, 124, 10298
7. Kerr, M. S.; Rovis, T. J. Am. Chem. Soc. 2004, 126, 8876
8. Pesch, J.; Harms, K.; Bach, T. Eur. J. Org. Chem. 2004, 2025
9. Mennen, S. M.; Blank, J. T.; Tran-Dubé, M. B.; Imbriglio, J. E.; Miller, S. J. Chem. Commun. 2005, 195
10. Mattson, A. E.; Bharadwaj, A. R.; Scheidt, K. A. J. Am. Chem. Soc. 2004, 126, 2314
11. Ballini, R.; Barboni, L.; Bosica, G.; Fiorini, D. Synthesis 2002, 2725
12. Custar, D. W.; Le, H.; Morken, J. P. Org. Lett. 2010, 12, 3760
13. Smith, A. B.; Adams, C. M. Acc. Chem. Res. 2004, 37, 365
14. Fernández, M.; Uria, U.; Vicario, J. L.; Reyes, E.; Carrillo, L. J. Am. Chem. Soc. 2012, 134, 11872
15. Shen, Z. -L.; Goh, K. K. K.; Cheong, H. -L.; Wong, C. H. A.; Lai, Y. -C.; Yang, Y. -S.; Loh, T. -P. J. Am. Chem. Soc. 2010, 132, 15852
16. Wender, P. A.; Erhardt, J. M.; Letendre, L. J. J. Am. Chem. Soc. 1981, 103, 2114
17. Lin, J.; Chan, W. H.; Lee, A. W. M.; Wong, W. Y. Tetrahedron 1999, 55, 13983
18. Miura, K.; Fujisawa, N.; Saito, H.; Wang, D.; Hosomi, A. Org. Lett. 2001, 3, 2591
19. Yasuda, M.; Tsuji, S.; Shigeyoshi, Y.; Baba, A. J. Am. Chem. Soc. 2002, 124, 7440
20. Korboukh, I.; Kumar, P.; Weinreb, S. M. J. Am. Chem. Soc. 2007, 129, 10342
21. Kumar, P.; Li, P.; Korboukh, I.; Wang, T. L.; Yennawar, H.; Weinreb, S. M. J. Org. Chem. 2011, 76, 2094
22. Sengupta, R.; Witek, J. A.; Weinreb, S. M. Tetrahedron 2011, 67, 8229
23. Witek, J. A.; Weinreb, S. M. Org. Lett. 2011, 13, 1258
24. Muthusamy, S.; Srinivasan, P. Tetrahedron Lett. 2006, 47, 6297
25. Ramig, K.; Kuzemko, M. A.; McNamara, K.; Cohen, T. J. Org. Chem. 1992, 57, 1968
26. Renaud, P.; Fox, M. A. J. Org. Chem. 1988, 53, 3745
27. Baran, P. S.; Hafensteiner, B. D.; Ambhaikar, N. B.; Guerrero, C. A.; Gallagher, J. D. J. Am. Chem. Soc. 2006, 128, 8678
28. Jang, H. -Y.; Hong, J. -B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2007, 129, 7004
29. Clift, M. D.; Thomson, R. J. J. Am. Chem. Soc. 2009, 131, 14579
30. Martin, C. L.; Overman, L. E.; Rohde, J. M. J. Am. Chem. Soc. 2010, 132, 4894
31. Casey, B. M.; Flowers, R. A. J. Am. Chem. Soc. 2011, 133, 11492
32. For instance, see: Rössle, M.; Werner, T.; Baro, A.; Frey, W.; Christoffers, J. Angew. Chem., Int. Ed. 2004, 43, 6547
33. Miller, E. J.; Zhao, W.; Herr, J. D.; Radosevich, A. T. Angew. Chem., Int. Ed. 2012, 51, 10605
34. Kukhtin, V. A. Dokl. Akad. Nauk SSSR 1958, 121, 466
35. Ramirez, F. Pure Appl. Chem. 1964, 9, 337
36. Ramirez, F. Acc. Chem. Res. 1968, 1, 168
37. Osman, F. H.; El-Samahy, F. A. Chem. Rev. 2002, 102, 629
38. Burger, K. Organophosphorus Reagents in Organic Synthesis; Cadogan, J. I. G., Ed.; Academic Press: London, U.K., 1979; pp 467-510.
39. McClure, C. K.; Jung, K.-Y. J. Org. Chem. 1991, 56, 867
40. McClure, C. K.; Grote, C. W. Tetrahedron Lett. 1991, 32, 5313
41. McClure, C. K.; Jung, K.-Y.; Grote, C. W.; Hansen, K. Phos. Sulfur Relat. Elem. 1993, 75, 23
42. McClure, C. K.; Mishra, P. Tetrahedron Lett. 2002, 43, 5249
43. Mark, V. J. Am. Chem. Soc. 1963, 85, 1884
44. Newman, M. S.; Blum, S. J. Am. Chem. Soc. 1964, 86, 5598
45. Griffin, G. W.; Gibson, D. M.; Ishikawa, K. J. Chem. Soc., Chem. Commun. 1975, 595
46. Griffin, G. W.; Gibson, D. M.; Ishikawa, K. J. Chem. Soc., Chem. Commun. 1976, 616
47. Muller, A. J.; Nishiyama, K.; Griffin, G. W.; Ishikawa, K.; Gibson, D. M. J. Org. Chem. 1982, 47, 2342
48. Ramirez, F.; Gulati, A. S.; Smith, C. P. J. Org. Chem. 1968, 33, 13
49. Liu, X.; Verkade, J. G. J. Org. Chem. 2000, 65, 4560
50. Corre, E.; Foucaud, A. J. Chem. Soc. D 1971, 570
51. Fauduet, H.; Burgada, R. Synthesis 1980, 642
52. Romanova, I. P.; Bogdanov, A. V.; Mironov, V. F.; Shaikhutdinova, G. R.; Larionova, O. A.; Latypov, S. K.; Balandina, A. A.; Yakhvarov, D. G.; Gubaidullin, A. T.; Saifina, A. F.; Sinyashin, O. G. J. Org. Chem. 2011, 76, 2548
53. Harpp, D. N.; Mathiaparanam, P. Tetrahedron Lett. 1970, 11, 2089
54. Harpp, D. N.; Mathiaparanam, P. J. Org. Chem. 1971, 36, 2540
55. Harpp, D. N.; Mathiaparanam, P. J. Org. Chem. 1972, 37, 1367
56. Zhang, W.; Shi, M. Chem. Commun. 2006, 1218
57. Shi, M.; Liu, X. -G.; Guo, Y. -W.; Zhang, W. Tetrahedron 2007, 63, 12731
58. For an intermolecular proton transfer to Kukhtin-Ramirez-like adducts, see: Griffiths, D. V.; Jamalia, H. A. R.; Tebby, J. C. Phos. Sulfur Relat. Elem. 1985, 25, 173
59. Kumara Swamy, K. C.; Bhuvan Kumar, N. N.; Balaraman, E.; Pavan Kumar, K. V. P. Chem. Rev. 2009, 109, 2551 and references therein
60. Castro, B. R. Org. React. 1983, 29, 1
61. Jung, C.-K.; Wang, J.-C.; Krische, M. J. J. Am. Chem. Soc. 2004, 126, 4118
62. Fan, R.-H.; Hou, X.-L.; Dai, L.-X. J. Org. Chem. 2004, 69, 689
63. Low, K. H.; Magomedov, N. A. Org. Lett. 2005, 7, 2003
64. McDougal, N. T.; Schaus, S. E. Angew. Chem., Int. Ed. 2006, 45, 3117
65. Lu, Y.; Arndtsen, B. A. Org. Lett. 2009, 11, 1369
66. Xu, S.; Zou, W.; Wu, G.; Song, H.; He, Z. Org. Lett. 2010, 12, 3556
67. Xie, P.; Huang, Y.; Chen, R. Chem.-Eur. J. 2012, 18, 7362
68. Wang, S. R.; Radosevich, A. T. Org. Lett. 2013, 15, 1926
69. Ianni, A.; Waldvogel, S. R. Synthesis 2006, 2103
70. Meng, Q.; Sun, Y.; Ratovelomanana-Vidal, V.; Geneît, J. P.; Zhang, Z. J. Org. Chem. 2008, 73, 3842
71. Creary, X. J. Org. Chem. 1987, 52, 5026
72. Anslyn, E. V.; Dougherty, D. A. Modern Physical Organic Chemistry; University Science: Sausalito, CA, 2006; p 651.
73. Schmittel, M. Top. Curr. Chem. 1994, 169, 183
74. Hintz, S.; Heidbreder, A.; Mattay, J. Top. Curr. Chem. 1996, 177, 77
75. Snider, B. B. Chem. Rev. 1996, 96, 339
76. Moeller, K. D. Top. Curr. Chem. 1997, 185, 49
77. Ischay, M. A.; Yoon, T. Eur. J. Org. Chem. 2012, 18, 3359
78. Wilsily, A.; Fillion, E. Org. Lett. 2008, 10, 2801
79. Dumas, A. M.; Fillion, E. Acc. Chem. Res. 2010, 43, 440