N-heterocyclic carbene-catalyzed amidation of unactivated esters with amino alcohols

Organic Letters

Volumn 7, Issue 12, 2005, Pages 2453-2456

  Movassaghi, Mohammad ^a   Schmidt, Michael A ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOALCOHOL; CARBENOID; ESTER DERIVATIVE; HETEROCYCLIC COMPOUND;

AMIDATION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; X RAY ANALYSIS;

EID: 20544443754     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol050773y     Document Type: Article

References (71)

1. (a) Benz, G. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 6, Chapter 2.3.
2. (b) Albericio, F.; Chinchilla, R.; Dodsworth, D. J.; Najera, C. Org. Prep. Proced. Int. 2001, 33, 203-303.
3. (a) Meyers, A. I.; Knaus, G.; Kamata, K.; Ford, M. E. J. Am. Chem. Soc. 1976, 98, 567-576.
4. (b) Larcheveque, M.; Ignatova, E.; Cuvigny, T. J. Organomet. Chem. 1979, 177, 5-15.
5. (c) Evans, D. A.; Takacs, J. M. Tetrahedron Lett. 1980, 21, 4233-4236.
6. (d) Evans, D. A.; Ennis, M. D.; Mathre, D. J. J. Am. Chem. Soc. 1982, 104, 1737-1739.
7. (e) Myers, A. G.; Yang, B. H.; Chen, H.; Gleason, J. L. J. Am. Chem. Soc. 1994, 116, 9361-9362.
8. (f) Hintermann, T.; Seebach, D. Helv. Chim. Acta 1998, 81, 2093-2126.
9. (a) Wipf, P. Chem. Rev. 1995, 95, 2115-2134.
10. (b) Jin, Z. Nat. Prod. Rep. 2003, 20, 584-605.
11. For reviews on transesterification, see: (a) Otera, J. Chem. Rev. 1993, 93, 1449-1470.
12. (b) Grasa, G. A.; Singh, R.; Nolan, S. P. Synthesis 2004, 7, 971-985.
13. For catalytic condensation of carboxylic acids and alcohols, see: (c) Ishihara, K.; Ohara, S.; Yamamoto, H. Science 2000, 290, 1140-1142.
14. For catalytic transamidation, see: (d) Eldred, S. E.; Stone, D. A.; Gellman, S. H.; Stahl, S. S. J. Am. Chem. Soc. 2003, 125, 3422-3423.
15. For a cyanide-catalyzed aminolysis of esters, see: Högberg, T.; Ström, P.; Ebner, M.; Rämsby, S. J. Org. Chem. 1987, 52, 2033-2036.
16. (e) For representative use of amino alcohols in amidation reactions, see: Arai, K.; Shaw, C.-h.; Nozawa, K.; Kawai, K.-i.; Nakajima, S. Tetrahedron Lett. 1987, 28, 441-442,
17. Diana, G. D.; Cutcliffe, D.; Oglesby, R. C.; Otto, M. J.; Mallamo, J. P.; Akullian, V.; McKinlay, M. A. J. Med. Chem. 1989, 32, 450-455,
18. and Myers, A. G.; Gleason, J. L.; Yoon, T.; Kung, D. W. J. Am. Chem. Soc. 1997, 119, 656-673.
19. (f) For an electrochemical method for benzoylation of amino alcohols, see: Arai, K.; Tamura, S.; Masumizu, T.; Kawai, K.-i.; Nakajima, S.; Ueda, A. Can. J. Chem. 1990, 68, 903-907.
20. For the first successful isolation of an NHC, see: (a) Arduengo, A. J., III; Harlow, R. L.; Kline, M. J. Am. Chem. Soc. 1991, 113, 361-363.
21. (b) Arduengo, A. J., III; Dias, H. V. R.; Harlow, R. L.; Kline, M. J. Am. Chem. Soc. 1992, 114, 5530-5534.
22. For early studies, see: (c) Wanzlick, H.-W.; Schikora, E. Angew. Chem. 1960, 72, 494.
23. (d) Wanzlick, H.-W.; Kleiner, H.-J. Angew. Chem. 1961, 73, 493.
24. (a) Bourissou, D.; Guerret, O.; Gabbai, F. P.; Bertrand, G. Chem. Rev. 2000, 100, 39-92.
25. (b) Carbene Chemistry. From Fleeting Intermediates to Powerful Reagents; Bertrand, G., Ed.; Marcel Dekker: New York, 2002.
26. (a) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18-29.
27. (b) Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290-1309.
28. (c) Yong, B. S.; Nolan, S. P. Chemtracts: Org. Chem. 2003, 16, 205-227.
29. (d) Burgess, K.; Perry, M. C. Tetrahedron: Asymmetry 2003, 14, 951-961.
30. (e) Kremzow, D.; Seidel, G.; Lehmann, C.; Fürstner, A. Chem. Eur. J. 2005, 11, 1833-1853.
31. (a) Breslow, R. J. Am. Chem. Soc. 1958, 80, 3719-3726.
32. (b) Stetter, H.; Kuhlmann, H. Synthesis 1975, 379-380.
33. (c) Murry, J. A.; Frantz, D. E.; Soheili, A.; Tillyer, R.; Grabowski, E. J. J.; Reider, P. J. J. Am. Chem. Soc. 2001, 123, 9696-9697.
34. (d) Burstein, C.; Glorius, F. Angew. Chem., Int. Ed. 2004, 43, 6205-6208.
35. (e) Sohn, S. S.; Rosen, E. L.; Bode, J. W. J. Am. Chem. Soc. 2004, 126, 14370-14371.
36. For reviews, see: (f) List, B. Tetrahedron 2002, 58, 5573-5590.
37. For reviews, see: (g) Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2004, 43, 5138-5175.
38. (h) Enders, D.; Balensiefer, T. Acc. Chem. Res. 2004, 37, 534-541.
39. (a) Steglich, W.; Höfle, G. Angew. Chem., Int. Ed. Engl. 1969, 8, 981-983.
40. (b) Vedejs, E.; Diver, S. T. J. Am. Chem. Soc. 1993, 115, 3358-3359.
41. (c) Ruble, J. C.; Fu, G. C. J. Org. Chem. 1996, 61, 7230-7231.
42. (a) Connor, E. F.; Nyce, G. W.; Myers, M.; Mock, A.; Hedrick, J. L. J. Am. Chem. Soc. 2002, 124, 914-915.
43. (b) Grasa, G. A.; Kissling, R. M.; Nolan, S. P. Org. Lett. 2002, 4, 3583-3586.
44. (c) Nyce, G. W.; Lamboy, J. A.; Connor, E. F.; Waymouth, R. M.; Hedrick, J. L. Org. Lett. 2002, 4, 3587-3590.
45. (d) Grasa, G. A.; Gueveli, T.; Singh, R.; Nolan, S. P. J. Org. Chem. 2003, 68, 2812-2819.
46. (e) Nyce, G. W.; Glauser, T.; Connor, E. F.; Moeck, A.; Waymouth, R. M.; Hedrick, J. L. J. Am. Chem. Soc. 2003, 125, 3046-3056.
47. (f) Singh, R.; Kissling, R. M.; Letellier, M.-A.; Nolan, S. P. J. Org. Chem. 2004, 69, 209-212.
48. (g) For resolution of alcohols using vinyl esters, see: Kano, T.; Sasaki, K.; Maruoka, K. Org. Lett. 2005, 7, 1347-1349.
49. (a) In the absence of 3, incubation of equimolar amounts of esters 1a and 1b with 2a at 23°C provides less than 2 and 1%, respectively, of the corresponding amides in 12 h.
50. tbutoxide in place of IMes (3) in the coupling of 1a and 2a gave 60 and 74% yield of 4aa, respectively. See Supporting Information.
51. Introduction of anhydrous lithium chloride (5 mol %) to the reaction mixture increases the rate of this coupling (Table 1, entries 2, 7, and 13).
52. N-Fmoc-protected glycine methyl ester was found to undergo deprotection in the presence of either 3 or 2a.
53. See Supporting Information for details.
54. (a) Ohta, S.; Hayakawa, S.; Okamoto, M. Tetrahedron Lett. 1984, 25, 5681-5684.
55. (b) Davies, D. H.; Hall, J.; Smith, E. H. J. Chem. Soc., Perkin Trans. 1 1989, 837-838.
56. 8.
57. For a review, see: Steiner, T. Angew. Chem., Int. Ed. 2002, 41, 48-76.
58. 6, 20 °C) are found at 219.4, and 120.9 ppm, respectively.
59. CD = 29.4 Hz) ppm, respectively.
60. In the case of the more acidic alcohols, i.e., trifluoroethanol, our preliminary spectroscopic data clearly indicate a greater degree of proton transfer and the presence of multiple equilibrating complexes that include imidazolium alkoxide derivatives.
61. (a) Arduengo, A. J., III; Gamper, S. F.; Tamm, M.; Calabrese, J. C.; Davidson, F.; Craig, H. A. J. Am. Chem. Soc. 1995, 117, 572-573.
62. (b) Alder, R. W.; Allen, P. R.; Williams, S. J. J. Chem. Soc., Chem. Commun. 1995, 1267-1268.
63. (c) Kim, Y.-J.; Streitwieser, A. J. Am. Chem. Soc. 2002, 124, 5757-5761.
64. (d) Filipponi, S.; Jones, J. N.; Johnson, J. A.; Cowley, A. H.; Grepioni, F.; Braga, D. Chem. Commun. 2003, 2716-2717.
65. For the structure of a carbene-diphenylamine complex, see: Cowan, J. A.; Clyburne, J. A. C.; Davidson, M. G.; Harris, R. L. W.; Howard, J. A. K.; Küpper, P.; Leech, M. A.; Richards, S. P. Angew. Chem., Int. Ed. 2002, 41, 1432-1434.
66. Anhydrous lithium chloride was not used in this experiment.
67. Kemp, D. S.; Vellaccio, F., Jr. J. Org. Chem. 1975, 40, 3464-3465.
68. For use of NHCs in asymmetric catalysis, see refs 7d and 8e in addition to: (a) Sheehan, J. C.; Hunneman, D. H. J. Am. Chem. Soc. 1966, 88, 3666-3667.
69. (b) Kerr, M. S.; Rovis, T. J. Am. Chem. Soc. 2004, 126, 8876-8877.
70. (c) Mennen, S. M.; Gipson, J. D.; Kim, Y. R.; Miller, S. J. J. Am. Chem. Soc. 2005, 127, 1654-1655.
71. (d) Chan, A.; Scheidt, K. A. Org. Lett. 2005, 7, 905-908.