Oxazaborolidinone-catalyzed enantioselective Diels-Alder reaction of acyclic α,β-unsaturated ketones

Journal of Organic Chemistry

Volumn 73, Issue 1, 2008, Pages 212-218

  Singh, Ram Shanker ^a   Adachi, Shinya ^a   Tanaka, Fumi ^a   Yamauchi, Toyonao ^a   Inui, Chieko ^a   Harada, Toshiro ^a  

^a KYOTO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACYCLIC ENONE DIENOPHILES; DIELS ALDER REACTIONS; KETONE DIENES; KETONE DIENOPHILES; LEWIS ACID CATALYSTS;

CATALYST ACTIVITY; ENANTIOSELECTIVITY; REACTION KINETICS; UNSATURATED COMPOUNDS;

KETONES;

1,3 BUTADIENE DERIVATIVE; 1,3 CYCLOHEXADIENE; ALKADIENE; BORON DERIVATIVE; HETEROCYCLIC COMPOUND; KETONE DERIVATIVE; LEWIS ACID; OXAZABOROLIDINONE; THREONINE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; DIELS ALDER REACTION; ENANTIOSELECTIVITY; REACTION ANALYSIS;

CATALYSIS; CYCLIZATION; HETEROCYCLIC COMPOUNDS, 1-RING; KETONES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 37549025330     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo702043g     Document Type: Article

References (53)

1. For recent reviews of enantioselective Diels-Alder reactions, see: (a) Maruoka, K. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000; p 467.
2. (b) Evans, D. A.; Johnson, J. S. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: New York, 1999; Vol. 3, p 1177.
3. (c) Oppolzer, W. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: New York, 1991; Vol. 5.
4. (d) Kagan, H. B.; Riant, O. Chem. Rev. 1992, 92, 1007.
5. (e) Dias, L. C. J. Braz. Chem. Soc. 1997, 8, 289.
6. (a) Corey, E. J. Angew. Chem., Int. Ed. 2002, 41, 1650 and references cited therein.
7. (b) Ishihara, K.; Gao, Q.; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 10412.
8. Evans, D. A.; Barnes, D. M.; Johnson, J. S.; Lectka, T.; Matt, P.; Miller, S. J.; Murry, J. A.; Norcross, R. D.; Shaughnessy, S. A.; Campos, K. R. J. Am Chem. Soc. 1999, 121, 7582.
9. (a) Ryu, D. H.; Lee, T. W.; Corey, E. J. J. Am. Chem. Soc. 2002, 124, 9992.
10. (b) Ryu, D. H.; Corey, E. J. J. Am. Chem. Soc. 2003, 125, 6388.
11. (c) Zhou, G.; Hu, Q.-Y.; Corey, E. J. Org. Lett. 2003, 5, 3979.
12. (d) Ryu, D. H.; Zhou, G.; Corey, E. J. J. Am. Chem. Soc. 2004, 126, 4800.
13. (e) Liu, D.; Canales, E.; Corey, E. J. J. Am. Chem. Soc. 2007, 129, 1498.
14. Hawkins, J. M.; Nambu, M.; Loren, S. Org. Lett. 2003, 5, 4293.
15. Futatsugi, K.; Yamamoto, H. Angew. Chem., Int. Ed. 2005, 44, 1484.
16. Other approaches for the asymmetric Diels-Alder reaction of ketone: (a) Chiral secondary amine catalyst: Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 2458.
17. (b) Wilson, R. M.; Jen, W. S.; MacMillan, D. W. C. J. Am. Chem. Soc. 2005, 127, 11616.
18. (c) Chiral Brønsted acid catalyst: Nakashima, D.; Yamamoto, H. J. Am. Chem. Soc. 2006, 128, 9626.
19. (d) Chiral transition metal Lewis acid: Rickerby, J.; Vallet, M.; Bernardinelli, G.; Viton, F.; Kündig, E. P. Chem. Eur. J. 2007, 13, 3354.
20. (a) Hu, Q.-Y.; Rege, P. D.; Corey, E. J. J. Am. Chem. Soc. 2004, 126, 5984.
21. (b) Hu, Q.-Y.; Zhou, G.; Corey, E. J. J. Am. Chem. Soc. 2004, 126, 13708.
22. (c) Zhou, G.; Corey, E. J. J. Am. Chem. Soc. 2005, 127, 11958.
23. (d) Snyder, S. A.; Corey, E. J. J. Am. Chem. Soc. 2006, 128, 740.
24. 3, see ref 4e.
25. (a) Hawkins, J. M.; Loren, S. J. Am. Chem. Soc. 1991, 113, 7794.
26. (b) Hawkins, J. M.; Loren, S.; Nambu, M. J. Am. Chem. Soc. 1994, 116, 1657.
27. (a) Harada, T.; Iwai, H.; Takatsuki, H.; Fujita, K.; Kubo, M.; Oku, A. Org. Lett. 2001, 3, 2101.
28. (b) Wang, X.; Harada, T.; Iwai, H.; Oku, A. Chirality 2003, 15, 28.
29. (c) Wang, X.; Adachi, S.; Iwai, H.; Takatsuki, H.; Fujita, K.; Kubo, M.; Oku, A.; Harada, T. J. Org. Chem. 2003, 68, 10046.
30. (d) Harada, T.; Adachi, S.; Wang, X. Org. Lett. 2004, 6, 4877.
31. Harada, T.; Kusukawa, T. Synlett 2007, 1823.
32. For preliminary accounts of this work, see: Singh, R. S.; Harada, T. Eur. J. Org. Chem. 2005, 3433.
33. Dinwiddie, J. G., Jr.; McManus, S. P. J. Org. Chem. 1963, 28, 2416.
34. The absolute structure of 7g was established by the crystallographic analysis. See the Supporting Information.
35. (a) Rücker, C.; Lang, D.; Sauer, J.; Frige, H.; Sustman, R. Chem. Ber. 1980, 113, 1663.
36. (b) Fringuelli, F.; Taticchi, A. Dienes in the Diels-Alder Reaction; Wiley & Sons: New York, 1990.
37. Hopkins, P. B.; Fuchs, P. L. J. Org. Chem. 1978, 43, 1208.
38. Jessup, P. J.; Petty, C. B.; Roos, J.; Overman, L. E. Org. Syn. Collect. 1988, 6, 95.
39. Brion, F. Tetrahedron Lett. 1982, 23, 5299.
40. 4-catalyzed reaction, see; Hayashi, Y.; Nakamura, M.; Nakao, S.; Inoue, T.; Shoji, M. Angew. Chem., Int. Ed. 2002, 41, 4079.
41. Corey, E. J.; Loh, T.-P. Tetrahedron Lett. 1993, 34, 3979.
42. Harada, T.; Yamamoto, Y.; Kusukawa, T. Chem. Commun. 2005, 859.
43. (a) Ishihara, K. In Lewis Acids in Organic Synthesis; Yamamoto, H., Ed.; Wiley-VCH: Weinheim, Germany, 2000; Vol. 1, p 135.
44. (b) Ishihara, K.; Yamamoto, H. Eur. J. Org. Chem. 1999, 527.
45. Houk, K. H.; Gonzalez, J.; Li. Y. Acc. Chem. Res. 1995, 28, 81.
46. (a) Itoh, K.; Kitoh, K.; Sera. A. Heterocycles 1999, 51, 243.
47. (b) Itoh, K.; Kitoh, K.; Kishimoto, S. Can. J. Chem. 2006, 84, 392.
48. (a) Domingo, L. R.; Picher, M. T.; Zaragozá, R. J. J. Org. Chem. 1998, 63, 9183.
49. (b) Domingo, L. R.; Picher, M. T.; Andrés, J.; Oliva, M. J. Org. Chem. 1999, 64, 3026.
50. (c) Domingo, L. R.; Picher, M. T.; Aurell. M. L. J. Phys. Chem. A 1999, 103, 11425.
51. If retro-Diels-Alder reaction were responsible for the endo-exo isomerization, complete racemization of exo-7v (entry 8) would be observed in full equilibrium, where the thermodynamically more stable exo isomer would be a major component.
52. 2O at room temperature gave a 48:52 mixture of endo-7v (64% ee) and ent-exo-7v (56% ee) in 31% yield.
53. Specific rotation was measured for the product of the reaction with OXB 3c (5 mol %) at -78°C for 0.3 h in toluene (34% yield, endo:exo = 86:14, endo; 96% ee, exo; 23% ee).