Asymmetric N-Heterocyclic carbene (NHC) catalyzed acyl anion reactions

Aldrichimica Acta

Volumn 44, Issue 1, 2011, Pages 3-11

  Vora, Harit U ^a   Rovis, Tomislav ^a  

^a Department of Environmental and Radiological Health Sciences   (United States)

Author keywords

Acyl anion; N heterocyclic carbene; NHC; Organocatalysis; Polarity reversal; Umpolung

Indexed keywords

EID: 79958213157     PISSN: 00025100     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (96)

1. Bertelsen, S.; Jørgensen, K. A. Chem. Soc. Rev. 2009, 38, 2178.
2. Gaunt, M. J.; Johansson, C. C. C.; McNally, A.; Vo, N. T. Drug Discovery Today 2007, 12, 8 and references therein.
3. Enders, D.; Niemeier, O.; Henseler, A. Chem Rev. 2007, 107, 5606.
4. Marion, N.; Díez-González, S.; Nolan, S. P. Angew. Chem., Int. Ed. 2007, 46, 2988.
5. Nair, V.; Vellalath, S.; Babu, B. P. Chem. Soc. Rev. 2008, 37, 2691.
6. Moore, J. L.; Rovis, T. Top. Curr. Chem. 2009, 291, 77.
7. Phillips, E. M.; Chan, A.; Scheidt, K. A. Aldrichimica Acta 2009, 42, 55.
8. Wöhler, F.; Liebig, J. Ann. Pharm. (presently part of Eur. J. Org. Chem.) 1832, 3, 249.
9. Ukai, T.; Tanaka, R.; Dokawa, T. J. Pharm. Soc. Jpn. (Yakugaku Zasshi) 1943, 63, 296.
10. Ukai, T.; Tanaka, R.; Dokawa, T. Chem. Abstr. 1951, 45, 29649.
11. Breslow, R. J. Am. Chem. Soc. 1958, 80, 3719.
12. Lapworth, A. J. Chem. Soc. 1903, 83, 995.
13. Carbene Chemistry: From Fleeting Intermediates to Powerful Reagents; Bertrand, G., Ed.; Marcel Dekker: New York, 2002.
14. Dixon, D. A.; Arduengo, A. J., III. J. Phys. Chem. 1991, 95, 4180.
15. Arduengo, A. J., III; Rasika Dias, H. V.; Harlow, R. L.; Kline, M. J. Am. Chem. Soc. 1992, 114, 5530.
16. Arduengo, A. J., III. Acc. Chem. Res. 1999, 32, 913.
17. Bauschlicher, C. W., Jr.; Schaefer, H. F., III; Bagus, P. S. J. Am. Chem. Soc. 1977, 99, 7106.
18. Wanzlick, H.-W. Angew. Chem., Int. Ed. Engl. 1962, 1, 75.
19. Arduengo, A. J., III; Harlow, R. L.; Kline, M. J. Am. Chem. Soc. 1991, 113, 361.
20. Sheehan, J. C.; Hunneman, D. H. J. Am. Chem. Soc. 1966, 88, 3666.
21. Sheehan, J. C.; Hara, T. J. Org. Chem. 1974, 39, 1196.
22. Tagaki, W.; Tamura, Y.; Yano, Y. Bull. Chem. Soc. Jpn. 1980, 53, 478.
23. Marti, J.; Castells, J.; López-Calahorra, F. Tetrahedron Lett. 1993, 34, 521.
24. Knight, R. L.; Leeper, F. J. Tetrahedron Lett. 1997, 38, 3611.
25. Gerhard, A. U.; Leeper, F. J. Tetrahedron Lett. 1997, 38, 3615.
26. Dvorak, C. A.; Rawal, V. H. Tetrahedron Lett. 1998, 39, 2925.
27. Enders, D.; Breuer, K.; Raabe, G.; Runsink, J.; Teles, J. H.; Melder, J.-P.; Ebel, K.; Brode, S. Angew. Chem., Int. Ed. Engl. 1995, 34, 1021.
28. Enders, D.; Breuer, K.; Teles, J. H. Helv. Chim. Acta 1996, 79, 1217.
29. Enders, D.; Kallfass, U. Angew. Chem., Int. Ed. 2002, 41, 1743.
30. Knight, R. L.; Leeper, F. J. J. Chem. Soc., Perkin Trans. 1 1998, 1891.
31. Stetter, H. Angew. Chem., Int. Ed. Engl. 1976, 15, 639.
32. Ciganek, E. Synthesis 1995, 1311.
33. Trost had previously demonstrated an intramolecular Stetter reaction en route to hirsutic acid: Trost, B. M.; Shuey, C. D.; DiNinno, F., Jr. J. Am. Chem. Soc. 1979, 101, 1284.
34. Enders, D.; Breuer, K.; Runsink, J.; Teles, J. H. Helv. Chim. Acta 1996, 79, 1899.
35. Kerr, M. S.; Read de Alaniz, J.; Rovis, T. J. Org. Chem. 2005, 70, 5725.
36. Vora, H. U.; Lathrop, S. P.; Reynolds, N. T.; Kerr, M. S.; Read de Alaniz, J.; Rovis, T. Org. Synth. 2010, 87, 350.
37. Read de Alaniz, J.; Rovis, T. Synlett 2009, 1189.
38. Note, however, that a Stetter-like process has been described for aldehydes bearing unactivated terminal alkenes; see: (a) He, J.; Zheng, J.; Liu, J.; She, X.; Pan, X. Org. Lett. 2006, 8, 4637.
39. He, J.; Tang, S.; Liu, J.; Su, Y.; Pan, X.; She, X. Tetrahedron 2008, 64, 8797.
40. Hirano, K.; Biju, A. T.; Piel, I.; Glorius, F. J. Am. Chem. Soc. 2009, 131, 14190.
41. Biju, A. T.; Wurz, N. E.; Glorius, F. J. Am. Chem. Soc. 2010, 132, 5970.
42. Kerr, M. S.; Read de Alaniz, J.; Rovis, T. J. Am. Chem. Soc. 2002, 124, 10298.
43. Kerr, M. S.; Rovis, T. Synlett 2003, 1934.
44. Reynolds, N. T.; Rovis, T. Tetrahedron 2005, 61, 6368.
45. Read de Alaniz, J.; Kerr, M. S.; Moore, J. L.; Rovis, T. J. Org. Chem. 2008, 73, 2033.
46. Cullen, S. C.; Rovis, T. Org. Lett. 2008, 10, 3141.
47. Kerr, M. S.; Rovis, T. J. Am. Chem. Soc. 2004, 126, 8876.
48. Moore, J. L.; Kerr, M. S.; Rovis, T. Tetrahedron 2006, 62, 11477.
49. Read de Alaniz, J.; Rovis, T. J. Am. Chem. Soc. 2005, 127, 6284.
50. Liu, Q.; Rovis, T. J. Am. Chem. Soc. 2006, 128, 2552.
51. Liu, Q.; Rovis, T. Org. Process Res. Dev. 2007, 11, 598.
52. Stetter, H.; Kuhlmann, H. Org. React. 1991, 40, 407. This chapter lists >500 examples of the Stetter reaction involving 93 different aldehydes. In terms of the Michael acceptor, the vast majority are unsubstituted at the β position, or are quite activated (maleates, fumarates, chalcones, etc.). Five examples contain simple alkyl substitution at the β position of the Michael acceptor [cyclopentenone (30% yield), pentenone (34% yield), and ethylidineacetoacetate (3 examples, 32-49% yields)].
53. Nahm, M. R.; Linghu, X.; Potnick, J. R.; Yates, C. M.; White, P. S.; Johnson, J. S. Angew. Chem., Int. Ed. 2005, 44, 2377.
54. Nahm, M. R.; Potnick, J. R.; White, P. S.; Johnson, J. S. J. Am. Chem. Soc. 2006, 128, 2751.
55. Mattson, A. E.; Bharadwaj, A. R.; Zuhl, A. M.; Scheidt, K. A. J. Org. Chem. 2006, 71, 5715.
56. Mattson, A. E.; Zuhl, A. M.; Reynolds, T. E.; Scheidt, K. A. J. Am. Chem. Soc. 2006, 128, 4932.
57. Enders, D.; Breuer, K. Addition of Acyl Carbanion Equivalents to Carbonyl Groups and Enones. In Comprehensive Asymmetric Catalysis I-III, Vol. 3; Jacobsen, E. N., Pfaltz, A., Yamamoto, H.; Springer-Verlag: Berlin, 1999; 1093-1102.
58. Enders, D.; Balensiefer, T. Acc. Chem. Res. 2004, 37, 534.
59. Enders, D.; Han, J.; Henseler, A. Chem. Commun. 2008, 3989.
60. Rovis, T. Chem. Lett. 2008, 37, 2.
61. Liu, Q.; Perreault, S.; Rovis, T. J. Am. Chem. Soc. 2008, 130, 14066.
62. Liu, Q.; Rovis, T. Org. Lett. 2009, 11, 2856.
63. DiRocco, D. A.; Oberg, K. M.; Dalton, D. M.; Rovis, T. J. Am. Chem. Soc. 2009, 131, 10872.
64. Wallach, O. Ber. Dtsch. Chem. Ges. (presently part of Eur. J. Inorg. Chem.) 1873, 6, 114.
65. Nowak, R. M. J. Org. Chem. 1963, 28, 1182.
66. Burns, N. Z.; Baran, P. S.; Hoffmann, R. W. Angew. Chem., Int. Ed. 2009, 48, 2854.
67. Amatore, M.; Beeson T. D.; Brown, S. P.; MacMillan, D. W. C. Angew. Chem., Int. Ed. 2009, 48, 5121 and references therein.
68. Reynolds, N. T.; Read de Alaniz, J.; Rovis, T. J. Am. Chem. Soc. 2004, 126, 9518.
69. Chow, K. Y.-K.; Bode, J. W. J. Am. Chem. Soc. 2004, 126, 8126.
70. Sohn, S. S.; Bode, J. W. Org. Lett. 2005, 7, 3873.
71. Chan, A.; Scheidt, K. A. Org. Lett. 2005, 7, 905.
72. Zeitler, K. Org. Lett. 2006, 8, 637.
73. Sohn, S. S.; Bode, J. W. Angew. Chem., Int. Ed. 2006, 45, 6021.
74. Mohr, J. T.; Hong, A. Y.; Stoltz, B. M. Nature Chem. 2009, 1, 359.
75. Reynolds, N. T.; Rovis, T. J. Am. Chem. Soc. 2005, 127, 16406.
76. Wack, H.; Taggi, A. E.; Hafez, A. M.; Drury, W. J., III; Lectka, T. J. Am. Chem. Soc. 2001, 123, 1531.
77. France, S.; Wack, H.; Taggi, A. E.; Hafez, A. M.; Wagerle, T. R.; Shah, M. H.; Dusich, C. L.; Lectka, T. J. Am. Chem. Soc. 2004, 126, 4245.
78. Lee, E. C.; McCauley, K. M.; Fu, G. C. Angew. Chem., Int. Ed. 2007, 46, 977.
79. Bruice, T. C.; Kundu, N. G. J. Am. Chem. Soc. 1966, 88, 4097.
80. Lienhard, G. J. Am. Chem. Soc. 1966, 88, 5642.
81. Owen, T. C.; Harris, J. N. J. Am. Chem. Soc. 1990, 112, 6136.
82. Owen, T. C.; Richards, A. J. Am. Chem. Soc. 1987, 109, 2520.
83. Han, C.; Lee, J. P.; Lobkovsky, E.; Porco, J. A., Jr. J. Am. Chem. Soc. 2005, 127, 10039.
84. Carpino, L. A. J. Am. Chem. Soc. 1993, 115, 4397.
85. Vora, H. U.; Rovis, T. J. Am. Chem. Soc. 2007, 129, 13796.
86. Bode, J. W.; Sohn, S. S. J. Am. Chem. Soc. 2007, 129, 13798.
87. Chiang, P.-C.; Kim, Y.; Bode, J. W. Chem. Commun. 2009, 4566.
88. Vora, H. U.; Moncecchi, J. R.; Epstein, O.; Rovis, T. J. Org. Chem. 2008, 73, 9727.
89. Czekelius, C.; Tzschucke, C. C. Synthesis 2010, 543 and references therein.
90. Takikawa, H.; Suzuki, K. Org. Lett. 2007, 9, 2713.
91. Vora, H. U.; Rovis, T. J. Am. Chem. Soc. 2010, 132, 2860.
92. Grondal, C.; Jeanty, M.; Enders, D. Nature Chem. 2010, 2, 167.
93. Lathrop, S. P.; Rovis, T. J. Am. Chem. Soc. 2009, 131, 13628.
94. Filloux, C. M.; Lathrop, S. P.; Rovis, T. Proc. Natl. Acad. Sci. U.S.A. 2010, 107, 20666.
95. Zhao, G.-L.; Córdova, A. Tetrahedron Lett. 2007, 48, 5976.
96. Jiang, H.; Gschwend, B.; Albrecht, L.; Jørgensen, K. A. Org. Lett. 2010, 12, 5052.