A new multicomponent reaction catalyzed by a [Lewis acid] +[Co(CO)4]- catalyst: Stereospecific synthesis of 1,3-oxazinane-2,4-diones from epoxides, isocyanates, and CO

Journal of the American Chemical Society

Volumn 129, Issue 26, 2007, Pages 8156-8162

  Church, Tamara L ^a   Byrne, Christopher M ^a   Lobkovsky, Emil B ^a   Coates, Geoffrey W ^a  

^a Department of Obstetrics Gynecology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON MONOXIDE; CARBONYLATION; EPOXIDATION; OPTIMIZATION; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

DIONES; EPOXIDES; ISOCYANATES; LACTONES;

CATALYSTS;

AZIRIDINE DERIVATIVE; CARBONYL DERIVATIVE; COBALT DERIVATIVE; EPOXIDE; IMINE; ISOCYANIC ACID DERIVATIVE; LACTONE DERIVATIVE; LEWIS ACID; OXAZINE DERIVATIVE; TETRAHYDROFURAN;

ARTICLE; BIOTRANSFORMATION; CARBONYLATION; CATALYSIS; CATALYST; COMPLEX FORMATION; CYCLIZATION; QUANTUM YIELD; REACTION ANALYSIS; RING CLOSING METATHESIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 34447125205     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja069065d     Document Type: Article

References (81)

1. For some leading references, see: (a) Leitner, A.; Shekhar, S.; Pouy, M. J.; Hartwig, J. F. J. Am. Chem. Soc. 2005, 127, 15506-15514.
2. (b) Williams, B. S.; Leatherman, M. D.; White, P. S.; Brookhart, M. J. Am. Chem. Soc. 2005, 127, 5132-5146.
3. (c) Nielsen, L. P. C.; Stevenson, C. P.; Blackmond, D. G.; Jacobsen, E. N. J. Am. Chem. Soc. 2004, 126, 1360-1362.
4. (d) Choi, T.-L.; Grubbs, R. H. Angew. Chem., Int. Ed. 2003, 42, 1743-1746.
5. (e) Noyori, R.; Hashiguchi, S. Acc. Chem. Res. 1997, 30, 97-102.
6. (f) Wai, J. S. M.; Markó, I.; Svendson, J. S.; Finn, M. G.; Jacobsen, E. N.; Sharpless, K. B. J. Am. Chem. Soc. 1989, 111, 1123-1125.
7. (a) Getzler, Y. D. Y. L.; Mahadevan, V.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc. 2002, 124, 1174-1175.
8. (b) Mahadevan, V.; Getzler, Y. D. Y. L.; Coates, G. W. Angew. Chem., Int. Ed. 2002, 41, 2781-2784.
9. (c) Getzler, Y. D. Y. L.; Mahadevan, V.; Lobkovsky, E. B.; Coates, G. W. Pure Appl. Chem. 2004, 76, 557-564.
10. (d) Schmidt, J. A. R.; Mahadevan, V.; Getzler, Y. D. Y. L.; Coates, G. W. Org. Lett. 2004, 6, 373-376.
11. (e) Schmidt, J. A. R.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc. 2005, 127, 11426-11435.
12. (f) Kramer, J. W.; Lobkovsky, E. B.; Coates, G. W. Org. Lett. 2006, 8, 3709-3712.
13. Church, T. L.; Getzler, Y. D. Y. L.; Coates, G. W. J. Am. Chem. Soc. 2006, 128, 10125-10133.
14. 2, which is isoelectronic with isocyanates, into Al-O bonds has been studied; see, for example: (a) Chisholm, M. H.; Zhou, Z. J. Am. Chem. Soc. 2004, 126, 11030-11039.
15. (b) Aida, T.; Inoue, S. J. Am. Chem. Soc. 1983, 105, 1304-1309.
16. (a) Feuillet, F. J. P.; Cheeseman, M.; Mahon, M. F.; Bull, S. D. Org. Biomol. Chem. 2005, 3, 2976-2989.
17. (b) Feuillet, F. J. P.; Robinson, D. E. J. E.; Bull, S. D. Chem. Commun. 2003, 2184-2185.
18. (c) Katagiri, N.; Hirose, M.; Sato, M.; Kaneko, C. Chem. Pharm. Bull. 1989, 37, 933-938.
19. Kamino, T.; Murata, Y.; Kawai, N.; Hosokawa, S.; Kobayashi, S. Tetrahedron Lett. 2001, 42, 5249-5252.
20. (a) Kende, A. S.; Kawamura, K.; DeVita, R. J. J. Am. Chem. Soc. 1990, 112, 4070-4072.
21. (b) Kende, A. S.; Kawamura, K.; Orwat, M. J. Tetrahedron Lett. 1989, 30, 5821-5824.
22. (a) Shibuya, I.; Goto, M.; Shimizu, M.; Yanagisawa, M.; Gama, Y. Heterocycles 1999, 51, 2667-2673.
23. (b) Paik, S.; Carmeli, S.; Cullingham, J.; Moore, R. E.; Patterson, G. M. L.; Tius, M. A. J. Am. Chem. Soc. 1994, 116, 8116-8125.
24. (c) Vorbrüggen, H. Tetrahedron Lett. 1968, 9, 1631-1634.
25. (d) Testa, E.; Fontanella, L.; Cristiani, G.; Gallo, G. J. Org. Chem. 1959, 24, 1928-1936.
26. (a) Kurz, T. Tetrahedron 2005, 61, 3091-3096.
27. (b) Kolasa, T.; Miller, M. J. Tetrahedron 1989, 45, 3071-3080.
28. (c) Pintye, J.; Fülöp, F.; Bernáth, G.; Sohár, P. Monatsch. Chem. 1985, 116, 857-868.
29. (d) Shapiro, S. L.; Rose, I. M.; Freedman, L. J. Am. Chem. Soc. 1957, 79, 2811-2814.
30. (a) Boontheung, P.; Perlmutter, P. Tetrahedron Lett. 1998, 39, 2629-2630.
31. (b) Ohshiro, Y.; Ando, N.; Komatsu, M.; Agawa, T. Synthesis 1985, 276-279.
32. (a) Lapkin, I. I.; Semenov, V. I.; Saitkulova, G. F. Russ. J. Org. Chem. 1982, 18, 2189.
33. (b) Saitkulova, F. G.; Semenov, V. I.; Lapkin, I. I. Khim. Elementoorg. Soedin. 1982, 22-26.
34. 2 has been reported to form OD; however, a large amount of α,β-unsaturated amide was also generated, possibly from decomposition of OD under the reaction conditions; see: Casadei, M. A.; Cesa, S.; Moracci, F. M.; Inesi, A.; Feroci, M. J. Org. Chem. 1996, 61, 380-383.
35. (a) Feuillet, F. J. P.; Niyadurupola, D. G.; Green, R.; Cheeseman, M.; Bull, S. D. Synlett 2005, 1090-1094.
36. (b) Ito, Y.; Terashima, S. Tetrahedron 1991, 47, 2821-2834.
37. (a) Yang, K.-S.; Chen, K. Org. Lett. 2002, 4, 1107-1109.
38. (b) Abbas, T. R.; Cadogan, J. I. G.; Doyle, A. A.; Gosney, I.; Hodgson, P. K. G.; Howells, G. E.; Hulme, A. N.; Parsons, S.; Sadler, I. H. Tetrahedron Lett. 1997, 38, 4917-4920.
39. (c) Narasaka, K.; Yamamoto, I. Tetrahedron 1992, 48, 5743-5754.
40. Barton, D. H. R.; Liu, W. Chem. Commun. 1997, 571-572.
41. Larksarp, C.; Alper, H. J. Org. Chem. 1999, 64, 9194-9200.
42. The reaction of phenols with N-(chlorocarbonyl)isocyanate, followed by intramolecular Friedel-Crafts reaction, has also been shown to form benzoxazinediones; see: Hagemann, H. Angew. Chem., Int. Ed. Engl. 1977, 16, 743-750.
43. A recent issue of Tetrahedron was devoted to multicomponent reactions: Tetrahedron 2005, 61, 11299-11519.
44. For reviews of transition-metal-mediated cycloaddition and heterocycle formation, including multicomponent examples: (a) Nakamura, I.; Yamamoto, Y. Chem. Rev. 2004, 104, 2127-2198.
45. (b) Fruhauf, H.-W. Chem. Rev. 1997, 97, 523-596.
46. (c) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49-92.
47. For some representative examples, see references 16, 18, and: (a) Kondo, T.; Nomura, M.; Ura, Y.; Wada, K.; Mitsudo, T.-A. J. Am. Chem. Soc. 2006, 128, 14816-14817.
48. (b) Siamaki, A. R.; Arndtsen, B. A. J. Am. Chem. Soc. 2006, 128, 6050-6051.
49. (c) Wegner, H. A.; de Meijere, A.; Wender, P. A. J. Am. Chem. Soc. 2005, 127, 6530-6531.
50. (d) Kamijo, S.; Jin, T.; Huo, Z.; Yamamoto, Y. J. Am. Chem. Soc. 2003, 125, 7786-7787.
51. (e) Cao, C.; Shi, Y.; Odom, A. L. J. Am. Chem. Soc. 2003, 125, 2880-2881.
52. (f) Goodman, S. N.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2002, 41, 4703-4705.
53. (g) Muraoka, T.; Kamiya, S.; Matsuda, I.; Itoh, K. Chem. Commun. 2002, 1284-1285.
54. (h) Dghaym, R. D.; Dhawan, R.; Arndtsen, B. A. Angew. Chem., Int. Ed. 2001, 40, 3228-3230.
55. (i) Montgomery, J. Acc. Chem. Res. 2000, 33, 467-473.
56. For several useful reviews, see: (a) Orru, R. V. A.; de Greef, M. Synthesis 2003, 10, 1471-1499.
57. (b) Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168-3210.
58. (c) Bienaymé, H.; Hulme, C.; Oddon, G.; Schmitt, P. Chem. - Eur. J. 2000, 6, 3321-3329.
59. (d) Armstrong, R. W.; Combs, A. P.; Tempest, P. A.; Brown, S. D.; Keating, T. A. Acc. Chem. Res. 1996, 29, 123-131.
60. (e) Posner, G. H. Chem. Rev. 1986, 86, 831-844.
61. CO = 300 psi, T = 25°C.
62. As 1 is only sparingly soluble in hexanes, stirring was essential to the success of the reaction.
63. Molnar, F.; Luinstra, G. A.; Allmendinger, M.; Rieger, B. Chem. - Eur. J. 2003, 9, 1273-1280.
64. See Supporting Information for details.
65. We were unable to separate OD 4ah′ from triethylisocyanurate.
66. Though most of the epoxide was unchanged following the reaction, small amounts of styrene and unidentified compounds were produced.
67. sBu.
68. Winstein, S.; Buckles, R. E. J. Am. Chem. Soc. 1942, 64, 2780-2786.
69. Smith, M. B.; March, J. March's Advanced Organic Chemistry, 5th ed.; John Wiley & Sons, Inc.: New York, 2001.
70. Using semiempirical methods, we have calculated the trans-ring-fused β-lactone from cyclopentene oxide to be approximately 45 kcal/mol higher in energy than the cis-ring-fused form (see ref 2e).
71. Sander, Maguire, and co-workers have reported observing trans-ring-fused 7-oxabicyclo[4.2.0]octan-8-one in an argon matrix using IR spectroscopy; see: Sander, W.; Strehl, A.; Maguire, A. R.; Collins, S.; Kelleher, P. G. Eur. J. Org. Chem. 2000, 3329-3335.
72. Getzler, Y. D. Y. L.; Kundnani, V.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc. 2004, 126, 6842-6843.
73. Silverstein, R. M.; Webster, F. X. Spectrometric Identification of Organic Compounds, 6 ed.; John Wiley & Sons, Inc.: New York, 1998.
74. C-H value.
75. 2e This reaction was proposed to occur via a cationic intermediate.
76. Flack, H. D. Acta Cryst. 1983, A39, 876-881.
77. Glass Contour Systems, Laguna Beach, CA, 92652.
78. Vyvyan, J. R.; Meyer, J. A.; Meyer, K. D. J. Org. Chem. 2003, 68, 9144-9147.
79. Mischitz, M.; Kroutil, W.; Wandel, U.; Faber, K. Tetrahedron: Asymmetry 1995, 6, 1261-1272.
80. Tokunaga, M.; Larrow, J. F.; Kakiuchi, F.; Jacobsen, E. N. Science 1997, 277, 936-938.
81. Noels, A. F.; Herman, J. J.; Teyssie, P. J. Org. Chem. 1976, 41, 2527-2531.