Stereo- And regioselectivity in an intramolecular nitrone-alkene cycloaddition of hept-6-enoses with a trans-acetonide blocking group

Chemistry - A European Journal

Volumn 15, Issue 11, 2009, Pages 2693-2707

  Shing, Tony K M ^a   Wong, Wai F ^a   Ikeno, Taketo ^b   Yamada, Tohru ^b  

^a CHINESE UNIVERSITY OF HONG KONG   (Hong Kong)

^b KEIO UNIVERSITY   (Japan)

Author keywords

Alkenes; Carbohydrates; Cycloaddition; Cycloheptanes; Nitrones

Indexed keywords

AMINES; CARBOHYDRATES; STEREOSELECTIVITY;

ALKENES; CYCLOADDUCTS; CYCLOHEPTANES; ISOPROPYLIDENE; NITRONE; NITRONES; TRANSITION STATE;

OLEFINS;

EID: 62349127208     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200800867     Document Type: Article

References (40)

1. a) A. E. Koumbis, J. K. Gallos, Curr. Org. Chem. 2003, 7, 585-628;
2. b) B. von Bernet, A. Vasella, Helv. Chem. Acta 1919, 62, 1990-2016;
3. c) T. K. M. Shing, D. A. Elsley, J. G. Gillhouley, J. Chem. Soc. Chem. Commun. 1989, 1280-1282.
4. J. J. Tufariello in 1,3-Dipolar Cycloaddition Chemistry, Vol.2 (Ed.: A. Padwa), Wiley. New York, 1984, pp. 83-168.
5. a) A. Roy, K. Chakrabarty, P. K. Dutta, N. C. Bar, N. Basu, B. Achari, S. B. Mandal, J. Org. Chem. 1999, 64, 2304-2309;
6. b) R. Patra, N. C. Bar, A. Roy, B. Achari, N. Ghoshal, S. B. Mandal, Tetrahedron 1996, 52, 11265-11272.
7. C. Gravier-Pelletier, W. Maton, T. Dintinger, C. Tellier, Y. L. Merrer, Tetrahedron 2003, 59, 8705-8720.
8. For recent syntheses, see: a) Y. Zhang, L. S. Liebeskind. J. Am. Chem. Soc. 2006, 128, 465-472;
9. b) D. M. Mans, W. H. Pearson, Org. Lett. 2004, 6, 3305-3308.
10. For recent syntheses, see: a) P. R. Skaanderup, R. Madsen, J. Org. Chem. 2003, 68, 2115-2122;
11. b) J. Marco-Contelles, E. de Opazo, J. Org. Chem. 2002, 67, 3705-3717.
12. a) B. Dräger. Nat. Prod. Rep. 2004, 21, 211-223;
13. b) N. Asano, Curr. Top. Med. Chem. 2003, 3, 471-484.
14. T. K. M. Shing, W. F. Wong, T. Ikeno, T. Yamada, Org. Lett. 2007, 9, 207-209.
15. T. K. M. Shing, A. W. F. Wong, T. Ikeno, T. Yamada, J. Org. Chem. 2006, 77, 3253-3263.
16. T. Gracza, T. Hasenöhrl, U. Stahl, V Jäger, Synthesis 1991, 1108-1118.
17. Y. L. Zhong, T. K. M. Shing, J. Org. Chem. 1997, 62, 2622-2624.
18. CCDC-242454, CCDC-614145, and CCDC-245397 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data- request/cif.
19. CCDC-261413 and CCDC-262043 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
20. CCDC-614146 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/ data-request/cif. Ref. [8] contains the experimental procedure for the debenzoylation and the relevant spectroscopic data.
21. Ref. [8] contains the spectroscopic data of cycloheptane 53.
22. J. S. Yadav, D. K. Barma, Tetrahedron 1996, 52, 4457-4466.
23. F. A. Luzzio, M. E. Menes, J. Org. Chem. 1994, 59, 7267-7272.
24. M. Frigerio, M Santagostino, S. Sputore, G. Palmisano, J. Org. Chem. 1995, 60, 7272-7276.
25. CCDC-607154 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/ data-request/cif.
26. [23e] because CONFLEX does not support the TS molecular mechanics (MM) model and the tricyclic structures investigated in this paper are relatively rigid, TSs were calculated based on the ground-state conformers: a) H. Goto, E. Osawa. J. Am. Chem. Soc. 1989, 111, 8950-8951;
27. b) H. Goto, E. Osawa, J. Chem. Soc. Perkin Trans. 2 1993, 187-198;
28. c) K. N. Houk, M. N. Paddon-row, N. G. Rondan, Y.-D. Wu, F.K. Brown, D. C. Spellmeyer, J. T. Mets, Y. Li, R. J. Loncharich. Science 1986, 231, 1108-1117.
29. a) A. D. Becke, J. Chem. Phys. 1993, 98, 5648;
30. b) C. T. Lee, W. T. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785.
31. Gaussian 98 (Revision A. 11), M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, Jr., R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, P. Salvador. J. J. Dannenberg, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, A. G. Baboul, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, J. L. Andres. C. Gonzalez, M. Head-Gordon, E. S. Replogle, J. A. Pople. Gaussian. Inc., Pittsburgh PA, 2001.
32. a) F. K. Brown, U. C. Singh, P. A. Kollman, L. Raimondi, K. N. Houk, C. W Bock, J. Org. Chem. 1992, 57, 4862-4869;
33. b) M. Carda, R. Portolés, J. Murga, S. Ureil, J. A. Marco, L. R. Domingo, R. J. Zaragozá, H. Röper. J. Org. Chem. 2000, 65, 7000-7009;
34. c) J. Liu, S. Niwayama, Y. You, K. N. Houk, J. Org. Chem. 1998, 63, 1064-1073;
35. d) E. C. Magnuson, J. Pranata, J. Comput. Chem. 1998, 19, 1795-1804;
36. e) R. Annunziata, M. Benaglia, M. Cinquini, F. Cozzi, L. Raimondi, Eur. J. Org. Chem. 1998, 1823-1832.
37. C. D. Valentin, M. Freccero, R. Gandolfi, A. Rastelli, J. Org. Chem. 2000, 65, 6112-6120.
38. J. B. Hendrickson, J. Am. Chem. Soc. 1961, 83, 4537-4547.
39. D. Batty, D. Crich, J. Chem. Soc. Perkin Trans. 1 1992, 3193-3204.
40. L. Zhu, D. R. Mootoo, Org. Lett. 2003, 5, 3475-3478.