On the [3 + 2] annulation of cyclic allylsilanes with N -phenyltriazolinedione: An enantio- and diastereoselective synthesis of cis -1,3-diaminocyclitols

Journal of Organic Chemistry

Volumn 75, Issue 13, 2010, Pages 4521-4529

  Dey, Raudra T ^a   Sarkar, Tarun K ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYLSILANES; DIASTEREOSELECTIVE SYNTHESIS; ENANTIO; STEREOCHEMICAL CONTROL; STEREOGENIC CENTERS;

SYNTHESIS (CHEMICAL);

AMINOCYCLITOL; SILANE DERIVATIVE; TRIAZOLINE DERIVATIVE;

ANNULATION REACTION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DIASTEREOISOMER; ENANTIOSELECTIVITY; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

ALKENES; CYCLITOLS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; SILANES; STEREOISOMERISM; TRIAZOLES;

EID: 77954123149     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo100724w     Document Type: Article

References (47)

1. Chapleur, Y. Carbohydrate Mimics; Wiley-VCH: Weinheim, 1998.
2. Mahmud, T. Nat. Prod. Rep. 2003, 20, 137-166
3. For some recent work, see: Mehta, G.; Lakshminath, S.; Talukdar, P. Tetrahedron Lett. 2002, 43, 335-338
4. Alegret, C.; Benet-Buchholz, J.; Riera, A. Org. Lett. 2006, 8, 3069-3072
5. Serrano, P.; Casas, J.; Zucco, M.; Emeric, G.; Egido-Gabás, M.; Llebaria, A.; Delgado, A. J. Comb. Chem. 2007, 9, 43-52
6. Pandey, G.; Tiwari, K. N.; Puranik, V. G. Org. Lett. 2008, 10, 3611-3614
7. Sakairi, N.; Hayashida, M.; Amano, A.; Kuzuhara, H. J. Chem. Soc., Perkin Trans.1 1990, 1301-1313
8. Schurrle, K.; Beier, B.; Piepersberg, W. J. Chem. Soc., Perkin Trans.1 1991, 2407-2412
9. Distler, J.; Klier, K.; Piendl, W.; Werbitzky, O.; Bock, A.; Kresze, G.; Piepersberg, W. FEMS Microbiol. Lett. 1985, 30, 145-150
10. Sepulchre, A. M.; Quiclet, B.; Gero, S. D. Bull. Soc. Chim. Fr. 1980, 1-2, 56-65
11. Rinehart, K. L., Jr. Pure Appl. Chem. 1977, 49, 1361-1384
12. Suami, T.; Shiio, T., Jap. Patent 61,286,396; Appl. 85/127 551, 12 June 1985
13. Chem. Abstr., 1986, 107, 191010p.
14. Bournaud, C.; Bonin, M.; Micouin, L. Org. Lett. 2006, 8, 3041-3043
15. Pérez Luna, A.; Ceschi, M.-A.; Bonin, M.; Micouin, L.; Husson, H.-P.; Gougeon, S.; Estenne-Bouhtou, G.; Marabout, B.; Sevrin, M.; George, P. J. Org. Chem. 2002, 67, 3522-3524
16. Bournaud, C.; Chung, F.; Pérez Luna, A.; Pasco, M.; Errasti, G.; Lecourt, T.; Micouin, L. Synthesis 2009, 869-887
17. Cong, X.; Liao, Q.-J.; Yao, Z.-J. J. Org. Chem. 2004, 69, 5314-5321
18. Knapp, S.; Patel, D. V. J. Am. Chem. Soc. 1983, 105, 6985-6986
19. For some early and pioneering work on [3 + 2] annulation of allylsilanes, see: Colvin, E. W.; Monteith, M. J. Chem. Soc., Chem. Commun. 1990, 1230-1232
20. Knölker, H.-J.; Jones, P. G.; Pannek, J.-B. Synlett 1990, 429-430
21. Danheiser, R. L.; Dixon, B. R.; Gleason, R. W. J. Org. Chem. 1992, 57, 6094-6097
22. Knölker, H.-J.; Foitzik, N.; Graf, R.; Goesmann, H. Angew. Chem., Int. Ed. 1993, 32, 1081-1083
23. Knölker, H.-J.; Graf, R. Tetrahedron Lett. 1993, 34, 4765-4768
24. Knölker, H.-J.; Foitzik, N.; Graf, R.; Pannek, J.-B.; Jones, P. G. Tetrahedron 1993, 49, 9955-9972
25. For some recent work on [3 + 2] annulation of allylsilanes, see: Romero, A.; Woerpel, K. A. Org. Lett. 2006, 8, 2127-2130
26. Dey, R. T.; Haque, Sk. A.; Hazra, A.; Basak, S.; Sarkar, T. K. Tetrahedron Lett. 2007, 48, 6671-6673
27. Schmidt, A. W.; Olpp, T.; Baum, E.; Stiffel, T.; Knölker, H.-J. Synlett 2007, 2371-2374
28. Huh, C. W.; Roush, W. R. Org. Lett. 2008, 10, 3371-3374
29. Orac, M. C.; Bergmeier, S. C. Tetrahedron Lett. 2009, 50, 1261-1263
30. Schmidt, A. W.; Olpp, T.; Schmid, S.; Jäger, A.; Knölker, H.-J. Tetrahedron 2009, 65, 5484-5490
31. For reviews on annulation reactions of allylsilanes, see: Masse, C. E.; Panek, J. S. Chem. Rev. 1995, 95, 1293-1316
32. Fleming, I.; Barbero, A.; Walter, D. Chem. Rev. 1997, 97, 2063-2192
33. Knölker, H.-J. J. Prakt. Chem. 1997, 339, 304-314
34. Chabaud, L.; James, P; Landais, Y. Eur. J. Org. Chem. 2004, 3173-3199
35. The configuration of the silyl group is based on our previous investigation in a related area. (11b)
36. Dang, H.-S.; Davies, A. G. J. Chem. Soc., Perkin Trans. 2 1991, 2011-2020
37. Cai, J.; Davies, A. G. J. Chem. Soc., Perkin Trans. 2 1992, 1743-1746
38. Yokoshima, S.; Tokuyama, H.; Fukuyama, T. Angew. Chem., Int. Ed. 2000, 39, 4073-4075
39. Clive, J. L. D.; Cheng, H.; Gangopadhyay, P.; Huang, X.; Prabhudas, B. Tetrahedron 2004, 60, 4205-4221
40. Lee, W. T.; Corey, E. J. Org. Lett. 2001, 3, 3337-3339
41. 4- o -OMe.
42. Heo, J.-N.; Micalizio, G. C.; Roush, W. R. Org. Lett. 2003, 5, 1693-1696
43. Clive, D. L. J.; Zhang, C.; Zhou, Y.; Tao, Y. J. Organomet. Chem. 1995, 489, C35-C37
44. Roberson, C. W.; Woerpel, K. A. J. Am. Chem. Soc. 2002, 124, 11342-11348
45. Fleming, I.; Henning, R.; Parker, D. C.; Plaut, H. E.; Sanderson, P. E. J. J. Chem. Soc., Perkin Trans. 1 1995, 317-337
46. Racherla, U. S.; Brown, H. C. J. Org. Chem. 1991, 56, 401-404
47. Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543-2549