N-heterocyclic carbene-catalyzed conjugate umpolung for the synthesis of γ-butyrolactones

Synthesis

Volumn , Issue 14, 2006, Pages 2418-2439

  Burstein, Christian ^a   Tschan, Serena ^a   Xie, Xiulan ^a   Glorius, Frank ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

Carbenes; Cyclization; Heterocycles; Lactones; Umpolung

Indexed keywords

ALDEHYDES; CATALYST ACTIVITY; KETONES; SYNTHESIS (CHEMICAL);

CARBENES; CYCLIZATION; HETEROCYCLES; LACTONES; UMPOLUNG;

ORGANIC COMPOUNDS;

ALPHA METHYLCINNAMALDEHYDE; CARBENE; CINNAMALDEHYDE DERIVATIVE; CROTONIC ACID DERIVATIVE; GAMMA BUTYROLACTONE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; SYNTHESIS;

EID: 33746584001     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-942447     Document Type: Article

References (88)

1. Seebach, D. Angew. Chem., Int. Ed. Engl. 1979, 18, 239.
2. For example the use of deprotonated dithianes as masked carbonyl anion synthons has become a very popular stoichiometric approach, see: Seebach, D.; Corey, E. J. J. Org. Chem. 1975, 40, 231.
3. (a) Eisch, J. J. J. Organomet. Chem. 1995, 500, 101.
4. (b) Pohl, M.; Lingen, B.; Müller, M. Chem. Eur. J. 2002, 8, 5288.
5. (a) Wöhler, F.; Liebig, J. Ann. Pharm. 1832, 3, 249.
6. (b) Lapworth, A. J. Chem. Soc. 1903, 83, 995.
7. (c) Breslow, R. J. Am. Chem. Soc. 1958, 80, 3719.
8. (a) Stetter, H.; Kuhlmann, H. Org. React. 1991, 40, 407.
9. (b) Stetter, H.; Kuhlmann, H. Chem. Ber. 1976, 109, 2890.
10. For excellent reviews, see: (a) Ahlbrecht, H.; Beyer, U. Synthesis 1999, 365.
11. (b) Hoppe, D. Angew. Chem., Int. Ed. Engl. 1984, 23, 932.
12. (c) Westiuk, N. Tetrahedron 1983, 39, 205. See also:
13. (d) Hoppe, D.; Zschage, O. Angew. Chem., Int. Ed. Engl. 1989, 28, 69.
14. (e) Zschage, O.; Hoppe, D. Tetrahedron 1992, 48, 5657.
15. For N-heterocyclic carbene catalyzed conjugate Umpolung and related reactions, see: (a) Chow, K. Y.-K.; Bode, J. W. J. Am. Chem. Soc. 2004, 126, 8126.
16. (b) Reynolds, N. T.; Read de Alaniz, J.; Rovis, T. J. Am. Chem. Soc. 2004, 126, 9518.
17. (c) Burstein, C.; Glorius, F. Angew. Chem. Int. Ed. 2004, 43, 6205.
18. (d) Sohn, S. S.; Rosen, E. L.; Bode, J. W. J. Am. Chem. Soc. 2004, 126, 14370.
19. (e) He, M.; Bode, J. W. Org. Lett. 2005, 7, 3131.
20. (f) Sohn, S. S.; Bode, J. W. Org. Lett. 2005, 7, 3873.
21. (g) Chan, A.; Scheldt, K. A. Org. Lett. 2005, 7, 905.
22. (h) Reynolds, N. T.; Rovis, T. J. Am. Chem. Soc. 2005, 127, 16406.
23. (i) Zeitler, K. Org. Lett. 2006, 8, 637. Very recently, the formation of spiro γ-butyrolactones by conjugate Umpolung using cyclic 1,2-diketones as the electrophiles was reported:
24. (j) Nair, V.; Vellalath, S.; Poonoth, M.; Mohan, R.; Suresh, E. Org. Lett. 2006, 8, 507.
25. For N-heterocyclic carbene catalyzed transesterification reactions, see: (a) Grasa, G. A.; Kissling, R. M.; Nolan, S. P. Org. Lett. 2002, 4, 3583.
26. (b) Grasa, G. A.; Guveli, T.; Singh, R.; Nolan, S. P. J. Org. Chem. 2003, 68, 2812.
27. (c) Singh, R.; Kissling, R. M.; Letellier, M.-A.; Nolan, S. P. J. Org. Chem. 2004, 69, 209.
28. (d) Singh, R.; Nolan, S. P. Chem. Commun. 2005, 5456.
29. (e) Nyce, G. W.; Lamboy, J. A.; Connor, E. F.; Waymouth, R. M.; Hedrick, J. L. Org. Lett. 2002, 4, 3587.
30. (f) Connor, E. F.; Nyce, G. W.; Myers, M.; Mock, A.; Hedrick, J. L. J. Am. Chem. Soc. 2002, 124, 914.
31. (g) Nyce, G. W.; Glauser, T.; Connor, E. F.; Mock, A.; Waymouth, R. M.; Hedrick, J. L. J. Am. Chem. Soc. 2003, 725, 3046. For a related amidation, see:
32. (h) Schmidt, M. A.; Movassaghi, M. Org. Lett. 2005, 7, 2453.
33. For the N-heterocyclic carbene catalyzed kinetic resolution of alcohols, see: (a) Suzuki, Y.; Yamauchi, K.; Muramatsu, K.; Sato, M. Chem. Commun. 2004, 2770.
34. (b) Kano, T.; Sasaki, K.; Maruoka, K. Org. Lett. 2005, 7, 1347.
35. For N-heterocyclic carbene catalyzed benzoin condensations, see: (a) Enders, D.; Niemeier, O.; Balensiefer, T. Angew. Chem. Int. Ed. 2006, 45, 1463.
36. (b) Enders, D.; Niemeier, O. Synlett 2004, 2111.
37. (c) Enders, D.; Kallfass, U. Angew. Chem. Int. Ed. 2002, 41, 1743.
38. (d) Hachisu, Y.; Bode, J. W.; Suzuki, K. J. Am. Chem. Soc. 2003, 125, 8432.
39. (e) Hachisu, Y.; Bode, J. W.; Suzuki, K. Adv. Synth. Catal. 2004, 346, 1097. See also:
40. (f) Dudding, T.; Houk, K. N. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5770.
41. (g) Pesch, J.; Harms, K.; Bach, T. Eur. J. Org. Chem. 2004, 2025.
42. For N-heterocyclic carbene catalyzed Steuer reactions, see: (a) Kerr, M. S.; Read de Alaniz, J.; Rovis, T. J. Am. Chem. Soc. 2002, 124, 10298.
43. (b) Kerr, M. S.; Rovis, T. J. Am. Chem. Soc. 2004, 126, 8876.
44. (c) Read de Alaniz, J.; Rovis, T. J. Am. Chem. Soc. 2005, 127, 6284.
45. (d) Mattson, A. E.; Bharadwaj, A. R.; Scheldt, K. A. J. Am. Chem. Soc. 2004, 126, 2314.
46. (e) Liu, Q.; Rovis, T. J. Am. Chem. Soc. 2006, 128, 2552.
47. (f) Braun, R. U.; Zeitler, K.; Müller, T. J. J. Org. Lett. 2001, 3, 3297.
48. (g) Bharadwaj, A. R.; Scheldt, K. A. Org. Lett. 2004, 6, 2465.
49. (h) Myers, M. C.; Bharadwaj, A. R.; Milgram, B. C.; Scheldt, K. A. J. Am. Chem. Soc. 2005, 127, 14675.
50. For some other N-heterocyclic carbene catalyzed reactions, see: (a) Suzuki, Y.; Toyota, T.; Imada, F.; Sato, M.; Miyashita, A. Chem. Commun. 2003, 1314.
51. (b) Song, J. J.; Tan, Z.; Reeves, J. T.; Gallou, F.; Yee, N. K.; Senanayake, C. H. Org. Lett. 2005, 7, 2193.
52. (c) Song, J. J.; Gallou, F.; Reeves, J. T.; Tan, Z.; Yee, N. K.; Senanayake, C. H. J. Org. Chem. 2006, 71, 1273.
53. (d) Duong, H. A.; Cross, M. J.; Louie, J. Org. Lett. 2004, 6, 4679.
54. (e) Mattson, A. E.; Scheldt, K. A. Org. Lett. 2004, 6, 4363.
55. (f) Fischer, C.; Smith, S. W.; Powell, D. A.; Fu, G. C. J. Am. Chem. Soc. 2006, 128, 1472.
56. For the stoichiometric use of N-heterocyclic carbenes as reagents, see: (a) Nair, V.; Bindu, S.; Sreekumar, V.; Rath, N. P. Org. Lett. 2003, 5, 665.
57. (b) Rigby, J. H.; Wang, Z. Org. Lett. 2002, 4, 4289.
58. (c) Enders, D.; Breuer, K.; Raabe, G.; Runsink, J.; Teles, J. H. Liebigs Ann. Chem. 1996, 2019.
59. (d) Nair, V.; Bindu, S.; Sreekumar, V. Angew. Chem. Int. Ed. 2004, 43, 5130.
60. (e) Ma, C.; Yang, Y. Org. Lett. 2005, 7, 1343.
61. For excellent reviews on N-heterocyclic carbenes in organocatalysis, see: (a) Enders, D.; Balensiefer, T. Acc. Chem. Res. 2004, 37, 534.
62. (b) Johnson, J. S. Angew. Chem. Int. Ed. 2004, 43, 1326.
63. (c) Christmann, M. Angew. Chem. Int. Ed. 2005, 44, 2632.
64. (d) Zeitler, K. Angew. Chem. Int. Ed. 2005, 44, 7506. For general reviews on N-heterocyclic carbenes, see:
65. (e) Hermann, W. A. Angew. Chem. Int. Ed. 2002, 41, 1291.
66. (f) Herrmann, W. A.; Köcher, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 2162.
67. (g) Arduengo, A. J. Ill; Krafczyk, R. Chem. Unserer Zeit 1998, 32, 6.
68. (h) Bourissou, D.; Guerret, O.; Gabbaï, F. P.; Bertrand, G. Chem. Rev. 2000, 100, 39.
69. (i) Perry, M. C.; Burgess, K. Tetrahedron: Asymmetry 2003, 14, 951.
70. (j) Cesar, V.; Bellemin-Laponnaz, S.; Gade, L. H. Chem. Soc. Rev. 2004, 33, 619.
71. For excellent reviews on modern organocatalysis, see: (a) Seayad, J.; List, B. Org. Biomol. Chem. 2005, 3, 719.
72. (b) Dalko, P. I.; Moisan, L. Angew. Chem. Int. Ed. 2004, 43, 5138.
73. (c) Dalko, P. I.; Moisan, L. Angew. Chem. Int. Ed. 2001, 40, 3726.
74. (d) Berkessel, A.; Gröger, H. Asymmetric Organocatalysis; VCH: Weinheim, 2004.
75. Under a different set of reaction conditions (t-BuOH, DBU, THF) and using two equivalents of electrophilic aldehyde, Bode et al. reported improved yields: ref. 7d.
76. 25 This data can be obtained free of charge from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; Fax: +44 (1223)336033; e-mail: deposit@ccdc.cam.ac.uk.
77. Bode et al. found that when using cis-cinnamaldehyde the same stereochemical outcome as with trans-cinnamaldehyde was observed. Moreover, stopping the reaction of cis-cinnamaldehyde prior to completion a significant amount of trans-cinnamaldehyde was observed, showcasing the importance of homoenolate resonance structure lib: ref. 7d.
78. (a) Glorius, F.; Altenhoff, G.; Goddard, R.; Lehmann, C. Chem. Commun. 2002, 2704. For the successful application of these ligands in the Suzuki cross-coupling of sterically hindered aryl chlorides, see:
79. (b) Altenhoff, G.; Goddard, R.; Lehmann, C. W.; Glorius, F. Angew. Chem. Int. Ed. 2003, 42, 3690.
80. (c) Altenhoff, G.; Goddard, R.; Lehmann, C. W.; Glorius, F. J. Am. Chem. Soc. 2004, 126, 15195.
81. Crotonaldehyde and a-methylcinnamaldehyde were reported to be unreactive under the conditions employed by Bode et al.: ref. 7 of ref. 7d.
82. For lactones in natural products, see: Seitz, M.; Reiser, O. Curr. Opin. Chem. Biol. 2005, 9, 285.
83. For the first step of the synthesis of aldehyde 23, see: (a) Boatman, S.; Harris, T. M.; Hauser, C. R. J. Org. Chem. 1965, 30, 3321. For the Heck reaction methodology used in the second step, see:
84. (b) Battistuzzi, G.; Cacchi, S.; Fabrizi, G. Org. Lett. 2003, 5, 777.
85. Stott, K.; Keeler, J.; Van Q, N.; Shaka, A. J. J. Magn. Reson. 1997, 125, 302.
86. Pearson, A. J.; Mesaros, E. F. Org. Lett. 2002, 4, 2001.
87. (a) Lehmann, C. W. private communication to the Cambridge Structural Database (2004), deposition numbers CCDC-246600 and 250238.
88. (b) Harms, K. private communication to the Cambridge Structural Database (2006), deposition numbers CCDC-603356 and 603357.