Utilization of aldoses as a carbonyl source in cyclocarbonylation of enynes

Journal of Organic Chemistry

Volumn 75, Issue 18, 2010, Pages 6279-6282

  Ikeda, Keiichi ^a   Morimoto, Tsumoru ^a   Kakiuchi, Kiyomi ^a  

^a NARA INSTITUTE OF SCIENCE AND TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

[CARBONYL; ASYMMETRIC VARIANTS; CARBONYL MOIETY; CYCLOCARBONYLATION; CYCLOPENTENONES; D-GALACTOSE; D-GLUCOSE; D-RIBOSE; D-XYLOSE; DIRECT USE; HIGH ENANTIOSELECTIVITY; RHODIUM CATALYSIS;

CARBON MONOXIDE; ENANTIOSELECTIVITY; GLUCOSE; RHODIUM; XYLOSE;

CARBONYLATION;

1,1' BINAPHTHYL DERIVATIVE; ALDEHYDE; ALDOSE; ALKYNE; CARBON MONOXIDE; CARBONYL DERIVATIVE; CYCLOPENTENONE; GALACTOSE; GLUCOSE; MANNOSE; MONOSACCHARIDE; RHODIUM; RIBOSE; UNCLASSIFIED DRUG; XYLOSE;

ARTICLE; ASYMMETRIC CATALYSIS; CARBONYLATION; CATALYST; CYCLIZATION; CYCLOCARBONYLATION; ENANTIOSELECTIVITY;

ALKYNES; CARBOHYDRATES; CATALYSIS; CYCLIZATION; KETONES; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; RHODIUM; STEREOISOMERISM;

EID: 77956551599     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo1012288     Document Type: Article

References (44)

1. For recent reviews of the Pauson-Khand reaction, see: Gibson, S. E.; Stevenazzi, A. Angew. Chem., Int. Ed. 2003, 42, 1800-1810
2. Shibata, T. Adv. Synth. Catal. 2006, 348, 2328-2336
3. Lee, H. W.; Kwong, F. Y. Eur. J. Org. Chem. 2010, 789-811
4. Morimoto, T.; Fuji, K.; Tsutsumi, K.; Kakiuchi, K. J. Am. Chem. Soc. 2002, 124, 3806-3807
5. Shibata, T.; Toshida, N.; Takagi, K. Org. Lett. 2002, 4, 1619-1621
6. Shibata, T.; Toshida, N.; Takagi, K. J. Org. Chem. 2002, 67, 7446-7450
7. Fuji, K.; Morimoto, T.; Tsutsumi, K.; Kakiuchi, K. Angew. Chem., Int. Ed. 2003, 42, 2409-2411
8. Jeong, N.; Kim, D. H.; Choi, J. H. Chem. Commun. 2004, 40, 1134-1135
9. Fuji, K.; Morimoto, T.; Tsutsumi, K.; Kakiuchi, K. Tetrahedron Lett. 2004, 45, 9163-9166
10. Kwong, F. Y.; Li, Y. M.; Lam, W. H.; Qiu, L.; Lee, H. W.; Yeung, C. H.; Chan, K. S.; Chan, A. S. C. Chem. - Eur. J. 2005, 11, 3872-3880
11. Shibata, T.; Toshida, N.; Yamasaki, M.; Maekawa, S.; Takagi, K. Tetrahedron 2005, 61, 9974-9979
12. Kwong, F. Y.; Lee, H. W.; Qiu, L.; Lam, W. H.; Li, Y.-M.; Kwong, H. L.; Chan, A. S. C. Adv. Synth. Catal. 2005, 347, 1750-1754
13. Kwong, F. Y.; Lee, H. W.; Lam, W. H.; Qiu, L.; Chan, A. S. C. Tetrahedron: Asymmetry 2006, 17, 1238-1252
14. Morimoto, T.; Fujioka, M.; Fuji, K.; Tsutsumi, K.; Kakiuchi, K. Pure Appl. Chem. 2008, 80, 1079-1087
15. Quite recently, Chung's group has reported on the use of alcohols as a carbonyl source in a rhodium-catalyzed cyclocarbonylation. In this case, aldehydes generated in situ via dehydrogenation of alcohols act as a carbonyl source: Park, J. H.; Cho, Y.; Chung, Y. K. Angew. Chem., Int. Ed. 2010, 49, 5138-5141
16. Park, K. H.; Son, S. U.; Chung, Y. K. Chem. Commun. 2003, 39, 1898-1899
17. Lee, H. W.; Chan, A. S. C.; Kwong, F. Y. Chem. Commun. 2007, 43, 2633-2635
18. For recent reviews, see: Hollingsworth, R. I.; Wang, G. Chem. Rev. 2000, 100, 4267-4282
19. Diéguez, M.; Pàmies, O.; Claver, C. Chem. Rev. 2004, 104, 3189-3215
20. Boysen, M. M. K. Chem. - Eur. J. 2007, 13, 8648-8659
21. For reviews, see: Inch, T. D. Adv. Carbohydr. Chem. Biochem. 1972, 27, 191-225
22. Hanessian, S. Acc. Chem. Res. 1979, 12, 159-165
23. Frase-Reid, B.; Sun, K. M.; Tam, T. F. Bull. Soc. Chim. Fr. 1981, 238-246
24. Inch, T. D. Tetrahedron 1984, 40, 3161-3213
25. Williams, N. R.; Davidson, B. E.; Ferrier, R. J.; Furneaux, R. H. Carbohydr. Chem. 1985, 17, 244-255
26. Nicolaou, K. C.; Mitchell, H. J. Angew. Chem., Int. Ed. 2001, 40, 1576-1624
27. For reports on decarbonylation of aldoses by a rhodium complex, see: Andrews, M. A.; Klaeren, S. A. J. Chem. Soc., Chem. Commun. 1988, 1266 - 1267 (stoichiometric).
28. Beck, R. H. F.; Elseviers, M.; Lemmens, H. O. J. EP 0716066A1, 1996, (stoichiometric).
29. Andrews, M. A. Organometallics 1989, 8, 2703 - 2708 (stoichiometric).
30. Andrews, M. A.; Gould, G. L.; Klaeren, S. A. J. Org. Chem. 1989, 54, 5257 - 5264 (stoichiometric).
31. Monrad, R. N.; Madsen, R. J. Org. Chem. 2007, 72, 9782 - 9785 (catalytic).
32. Oh, C. H.; Sung, H. R.; Jung, S. H.; Lim, Y. M. Tetrahedron Lett. 2001, 42, 5493-5495
33. Yamamoto, Y.; Kuwabara, S.; Ando, Y.; Nagata, H.; Nishiyama, H.; Itoh, K. J. Org. Chem. 2004, 69, 6697-6705
34. Chopade, P. R.; Louie, J. Adv. Synth. Catal. 2006, 348, 2307-2327
35. Shibata, T.; Otomo, M.; Tahara, Y.; Endo, K. Org. Biomol. Chem. 2008, 6, 4296-4298
36. 2O or 1-butanol as a solvent, which can dissolve at the reaction temperature, afforded no carbonylated product.
37. For the first step, see: Robert, S. W.; Rainier, J. D. Org. Lett. 2007, 9, 2227-2230 For the second step, see: Sim, M. M.; Kondo, H.; Wong, C. H. J. Am. Chem. Soc. 1993, 115, 2260-2267
38. Kim, D. E.; Kim, I. S.; Ratovelomanana-Vidal, V.; Genet, J.-P.; Jeong, N. J. Org. Chem. 2008, 73, 7985 - 7989.
39. For the synthesis of 2c and 2d, see ref 9. For the synthesis of 2e and 2f, see: Itoh, T.; Takamura, H.; Watanabe, K.; Araki, Y.; Ishido, Y. Carbohydr. Res. 1986, 156, 241-246
40. Bunten, K. A.; Farrer, D. H.; Poe, A. J.; Lough, A. Organometallics 2002, 21, 3344-3350 synthesis of RhCl(CO((S)-BINAP
41. For entry 18, 29% yield (32% recovery) and 86% ee; for entry 20, 31% yield (29% recovery) and 71% ee.
42. Madsen has described the similar discussion on the rhodium-catalyzed decarbonylation of aldoses in the previous report. See ref 6e.
43. At present, we have failed unfortunately to recover the decarbonylated residue.
44. For example, the acyclic aldehyde form of d -glucose exists only 0.019% in aqueous solution. See: Maple, R. R.; Allerhand, A. J. Am. Chem. Soc. 1987, 109, 3168-3169