Rhodium-catalyzed asymmetric reductive cyclization of heteroatom-linked 5-alkynals with heteroatom-substituted acetaldehydes

Journal of the American Chemical Society

Volumn 132, Issue 4, 2010, Pages 1238-1239

  Tanaka, Rie ^a   Noguchi, Keiichi ^a   Tanaka, Ken ^a  

^a TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL EQUATIONS; GOOD YIELD; HETEROATOMS; REDUCTIVE CYCLIZATION; RHODIUM-CATALYZED;

ALDEHYDES; ENANTIOSELECTIVITY; RHODIUM;

CYCLIZATION;

ACETALDEHYDE; ALKYNE DERIVATIVE; RHODIUM;

ARTICLE; ASYMMETRIC CATALYSIS; CATALYST; CYCLIZATION; ENANTIOSELECTIVITY; HYDROGEN BOND; QUANTUM YIELD; REACTION ANALYSIS; REDUCTION;

EID: 77950339390     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja9104655     Document Type: Article

References (35)

1. Selected reviews: (a) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635.
2. (b) Montgomery, J. Acc. Chem. Res. 2000, 33, 467.
3. (c) Montgomery, J. Angew. Chem., Int. Ed. 2004, 43, 3890.
4. (d) Jang, H.-Y.; Krische, M. J. Acc. Chem. Res. 2004, 37, 653.
5. (e) Fujiwara, M.; Ojima, I. Modern Rhodium-Catalyzed Organic Reactions; Evans, P. A., Ed.; Wiley-VCH: Weinheim, Germany, 2005; p 129.
6. (f) Miura, T.; Murakami, M. Chem. Commun. 2007, 217.
7. (g) Moslin, R. M.; Miller-Moslin, K.; Jamison, T. F. Chem. Commun. 2007, 4441.
8. (a) Oblinger, E.; Montgomery, J. J. Am. Chem. Soc. 1997, 119, 9065.
9. (b) Tang, X.-Q.; Montgomery, J. J. Am. Chem. Soc. 1999, 121, 6098.
10. (c) Tang, X.-Q.; Montgomery, J. J. Am. Chem. Soc. 2000, 122, 6950.
11. (d) Mahandru, G. M.; Liu, G.; Montgomery, J. J. Am. Chem. Soc. 2004, 126, 3698.
12. (e) Knapp-Reed, B.; Mahandru, G. M.; Montgomery, J. J. Am. Chem. Soc. 2005, 127, 13156.
13. (a) Ojima, I.; Tzamarioudaki, M.; Tsai, C.-Y. J. Am. Chem. Soc. 1994, 116, 3643.
14. (b) Bennacer, B.; Fujiwara, M.; Lee, S.-Y.; Ojima, I. J. Am. Chem. Soc. 2005, 127, 17756.
15. (c) Rhee, J. U.; Krische, M. J. J. Am. Chem. Soc. 2006, 128, 10674.
16. (d) Rhee, J. U.; Jones, R. A.; Krische, M. J. Synthesis 2007, 3427.
17. Patman, R. L.; Chaulagain, M. R.; Williams, V. M.; Krische, M. J. J. Am. Chem. Soc. 2009, 131, 2066.
18. Crowe, W. E.; Rachita, M. J. J. Am. Chem. Soc. 1995, 117, 6787.
19. (a) Oblinger, E.; Montgomery, J. J. Am. Chem. Soc. 1997, 119, 9065.
20. (b) Ni, Y.; Amarasinghe, K. K. D.; Montgomery, J. Org. Lett. 2002, 4, 1743.
21. (c) Patel, S. J.; Jamison, T. F. Angew. Chem., Int. Ed. 2003, 42, 1364.
22. (d) Patel, S. J.; Jamison, T. F. Angew. Chem., Int. Ed. 2004, 43, 3941.
23. (a) Shintani, R.; Okamoto, K.; Otomaru, Y.; Ueyama, K.; Hayashi, T. J. Am. Chem. Soc. 2005, 127, 54.
24. (b) Miura, T.; Shimada, M.; Murakami, M. Synlett 2005, 667.
25. (c) Matsuda, T.; Makino, M.; Murakami, M. Angew. Chem., Int. Ed. 2005, 44, 4608.
26. (d) Miura, T.; Shimada, M.; Murakami, M. Angew. Chem., Int. Ed. 2005, 44, 7598.
27. (e) Miura, T.; Shimada, M.; Murakami, M. Tetrahedron 2007, 63, 6131.
28. Tsukamoto, H.; Ueno, T.; Kondo, Y. J. Am. Chem. Soc. 2006, 128, 1406.
29. Hojo, M.; Murakami, Y.; Aihara, H.; Sakuragi, R.; Baba, Y.; Hosomi, A. Angew. Chem., Int. Ed. 2001, 40, 621.
30. (a) Tang, J.; Okada, K.; Shinokubo, H.; Oshima, K. Tetrahedron 1997, 53, 5061.
31. (b) Yorimitsu, H.; Tang, J.; Okada, K.; Shinokubo, H.; Oshima, K. Chem. Lett. 1998, 27, 11.
32. Takeishi, K.; Sugishima, K.; Sasaki, K.; Tanaka, K. Chem.-Eur. J. 2004, 10, 5681.
33. Cobalt-mediated [2 + 2 + 2] cycloaddition of 5-hexynal with bis(trimethylsilyl) acetylene has been reported: Harvey, D. F.; Johnson, B. M.; Ung, C. S.; Vollhardt, K. P. C. Synlett 1989, 15.
34. Intramolecular hydroacylation products were generated in 20-50% yield, except for unidentified mixtures of byproducts in entries 1-3, although these hydroacylation products could not be isolated in pure forms.
35. Homoreductive cyclization products 3 were generated in 5-30% yield, except for cross-reductive cyclization products 5.