Diastereoselective synthesis of tetrahydrofurans by Lewis acid catalyzed intermolecular carbenoid-carbonyl reaction-cycloaddition sequences: Unusual diastereoselectivity of Lewis acid catalyzed cycloadditions

Journal of Organic Chemistry

Volumn 78, Issue 12, 2013, Pages 6182-6195

  Hashimoto, Yuta ^a   Itoh, Kennosuke ^a   Kakehi, Akikazu ^a   Shiro, Motoo ^b   Suga, Hiroyuki ^a  

^a SHINSHU UNIVERSITY   (Japan)

^b RIGAKU CORPORATION   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC ALDEHYDE; DIASTEREO-SELECTIVITY; DIASTEREOSELECTIVE SYNTHESIS; DIASTEREOSELECTIVITIES; DIPOLE DIPOLE INTERACTIONS; TETRA-HYDROFURAN; TETRAFLUOROBORATES; THREE COMPONENT REACTIONS;

CATALYSIS; CYCLOADDITION; NICKEL;

STEREOSELECTIVITY;

(S) 3 (2 ALKENOYL) 4 ISOPROPYL 2 OXAZOLIDINONE; 1,3 DIOXOLANE; 2 OXAZOLIDINONE DERIVATIVE; 3 (2 ALKENOYL) 2 OXAZOLIDINONE; ALDEHYDE; ALKYL GROUP; ALPHA ALKYLALPHA DIAZO ESTER; CARBENOID; CARBONYL DERIVATIVE; LEWIS ACID; TETRAHYDROFURAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CYCLOADDITION; STEREOCHEMISTRY; SYNTHESIS; X RAY ANALYSIS;

EID: 84879360958     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo400858u     Document Type: Article

References (41)

1. Suga, H.; Inoue, K.; Inoue, S.; Kakehi, A. J. Am. Chem. Soc. 2002, 124, 14836
2. Suga, H.; Inoue, K.; Inoue, S.; Kakehi, A.; Shiro, M. J. Org. Chem. 2005, 70, 47
3. Suga, H.; Suzuki, T.; Inoue, K.; Kakehi, A. Tetrahedron 2006, 62, 9218
4. Suga, H.; Ishimoto, D.; Higuchi, S.; Ohtsuka, M.; Arikawa, T.; Tsuchida, T.; Kakehi, A.; Baba, T. Org. Lett. 2007, 9, 4359
5. Suga, H.; Higuchi, S.; Ohtsuka, M.; Ishimoto, D.; Arikawa, T.; Hashimoto, Y.; Misawa, S.; Tsuchida, T.; Kakehi, A.; Baba, T. Tetrahedron 2010, 66, 3070
6. MacMills, M. C.; Wright, D. In Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products; Padwa, A.; Pearson, W. H., eds.; Wiley: Hoboken, NJ, 2003; Chapter 4, p 253.
7. Padwa, A.; Weingarten, M. D. Chem. Rev. 1996, 96, 223
8. Padwa, A.; Hornbuckle, S. F. Chem. Rev. 1991, 91, 263
9. de March, P.; Huisgen, R. J. Am. Chem. Soc. 1982, 104, 4952
10. Nair, V.; Mathai, S.; Nair, S. M.; Rath, N. P. Tetrahedron Lett. 2003, 44, 8407
11. Lu, C.-D.; Chen, Z.-Y.; Liu, H.; Hu, W.-H.; Mi, A.-Q. Org. Lett. 2004, 6, 3071
12. Nair, V.; Mathai, S.; Mathew, S. C.; Rath, N. P. Tetrahedron 2005, 61, 2849
13. de March, P.; Huisgen, R. J. Am. Chem. Soc. 1982, 104, 4953
14. Alt, M.; Mass, G. Tetrahedron 1994, 50, 7435
15. Skaggs, A. J.; Lin, E. Y.; Jamison, T. F. Org. Lett. 2002, 4, 2277
16. Nair, V.; Mathai, S.; Varma, R. L. J. Org. Chem. 2004, 69, 1413
17. Lu, C.-D.; Chen, Z.-Y.; Liu, H.; Hu, W.-H.; Mi, A.-Q.; Doyle, M. P. J. Org. Chem. 2004, 69, 4856
18. Muthusamy, S.; Gunanathan, C.; Nethaji, M. J. Org. Chem. 2004, 69, 5631
19. Taber, D. F.; Herr, R. J.; Pack, S. K.; Geremia, J. M. J. Org. Chem. 1996, 61, 2908
20. DeAngelis, A.; Panne, P.; Yap, G. P. A.; Fox, J. M. J. Org. Chem. 2008, 73, 1435
21. Panne, P.; Fox, J. M. J. Am. Chem. Soc. 2007, 129, 22
22. Panne, P.; DeAngelis, A.; Fox, J. M. Org. Lett. 2008, 10, 2987
23. DeAngelis, A.; Taylor, M. T.; Fox, J. M. J. Am. Chem. Soc. 2009, 131, 1101
24. Evans, D. A.; Chapman, K. T.; Bisaha, J. J. Am. Chem. Soc. 1988, 110, 1238
25. Castellino, S. J. Org. Chem. 1990, 55, 5197
26. Sibi, M. P. Aldrichim. Acta 1999, 32, 93
27. Tsuge, O.; Kanemasa, S.; Yoshioka, M. J. Org. Chem. 1988, 53, 1384
28. Pandey, G.; Banerjee, P.; Gadre, S. R. Chem. Rev. 2006, 106, 4484
29. Adrio, J.; Carretero, J. C. Chem. Commun. 2011, 47, 6784
30. Sibi, M. P.; Soeta, T.; Jasperse, C. P. Org. Lett. 2009, 11, 5366 and references therein
31. Castellino, S.; Dwight, W. J. J. Am. Chem. Soc. 1993, 115, 2986
32. Castellino, S. J. Org. Chem. 1990, 55, 5197
33. Kanemasa, S.; Kanai, T. J. Am. Chem. Soc. 2000, 122, 10710
34. Itoh, K.; Hasegawa, M.; Tanaka, J.; Kanemasa, S. Org. Lett. 2005, 7, 979
35. Sibi, M. P.; Itoh, K.; Jasperse, C. P. J. Am. Chem. Soc. 2004, 126, 5366
36. Cai, C.; Soloshonok, V. A.; Hruby, V. J. J. Org. Chem. 2001, 66, 1339
37. Narasaka, K.; Iwasawa, N.; Inoue, M.; Yamada, T.; Nakashima, M.; Sugimori, J. J. Am. Chem. Soc. 1989, 111, 5341
38. Evans, D. A.; Chapman, K. T.; Bisaha, J. J. Am. Chem. Soc. 1988, 110, 1238
39. Galatsis, P.; Millan, S. D.; Ferguson, G. J. Org. Chem. 1997, 62, 5048
40. Cotton, F. A.; Felthouse, T. R. Inorg. Chem. 1980, 19, 323
41. Taber, D. F.; Sheth, R. B.; Joshi, P. V. J. Org. Chem. 2005, 70, 2851