Condensation-ring expansion reaction of formyl[2.2.1]bicyclic carbinols with para-substituted phenyl amines: Application to the preparation of [3.2.1]bicyclic n-aryl-1,2,3-oxathiazolidine-2-oxide agents

Journal of the Chinese Chemical Society

Volumn 59, Issue 3, 2012, Pages 378-388

  Yang, Te Fang ^a   Chen, Li Hsun ^b   Kao, Li Ta ^b   Chuang, Chih Hsiang ^a   Chen, Yong Yen ^a  

^a NATIONAL CHI NAN UNIVERSITY   (Taiwan)

^b CHAOYANG UNIVERSITY OF TECHNOLOGY   (Taiwan)

Author keywords

1,2,3 Oxathiazolidine 2 oxide; Bicyclic aryl amino ketone; Formyl bicyclic crbinols; Ring expansion

Indexed keywords

EID: 84859377959     PISSN: 00094536     EISSN: 21926549     Source Type: Journal    
DOI: 10.1002/jccs.201100517     Document Type: Article

References (24)

1. Stevens, C. L.; Ash, A. B.; Thuillier, A.; Amin, J. H.; Balys, A.; Dennis, W. E.; Dickerson, J. P.; Glinski, R. P.; Hanson, H. T.; Pillai, M. D.; Stoddard, J. W. J. Org. Chem. 1966, 31, 2593-2601.
2. Stevens, C. L.; Thuillier, A.; Daniher, F. A. J. Org. Chem. 1965, 30, 2962-2966.
3. Stevens, C. L.; Elliott, R. D.; Winch, B. L. J. Am. Chem. Soc. 1963, 85, 1464-1470.
4. Brunner, H.; Kagan, H. B.; Kreutzer, G. Tetrahedron: Asymmetry 2003, 14, 2177-2187.
5. Preiss, D. Patent DE 44 09 671 C1, 1995.
6. Menzer, M.; Kazmirowski, H.-G.; Moller, G.; Laban, G. Patent DD 217 511 A1, 1985.
7. Compain, P.; Gore, J.; Vatele, J.-M. Tetrahedron 1996, 52, 6647-6664.
8. Compain, P.; Gore, J.; Vatele, J.-M. Tetrahedron Lett. 1995, 36, 4059-4062.
9. Compain, P.; Gore, J.; Vatele, J.-M. Tetrahedron Lett. 1995, 36, 4063-4064.
10. Yang, T.-F.; Zhang, Z.-N.; Tseng, C.-H.; Chen, L.-H. Tetrahedron Lett. 2005, 46, 1917-1920.
11. Yang, T.-F.; Tseng, C.-H.; Wu, K.-I.; Chang, C.-N. J. Org. Chem. 2007, 72, 7034-7037.
12. Yang, T.-F.; Tseng, C.-H.; Shen, C.-H.; Chen, L.-H.; Kao, L.-T. Tetrahedron 2009, 65, 9854-9861.
13. Yang, T.-F.; Shen, C.-H.; Hsu, C.-T.; Chen, L.-H, ; Chuang, C.-H. Tetrahedron 2010, 66, 8734-8738.
14. Wudl, F.; Lee, T. B. K. J. Am. Chem. Soc. 1973, 95, 6349-6358.
15. Han, Z.; Krishnamurthy, D.; Grover, P.; Fang, Q. K.; Senanayake, C. H. J. Am. Chem. Soc. 2002, 124, 7880-7881.
16. Han, Z.; Krishnamurthy, D.; Grover, P.; Wilkinson, H. S.; Fang, Q. K.; Su, X.; Lu, Z.-H.; Magiera, D.; Senanayake, C. H. Angew. Chem., Int. Ed. 2003, 42, 2032-2035.
17. Han, Z.; Krishnamurthy, D.; Grover, P.; Fang, Q. K.; Su, X.; Wilkinson, H. S.; Lu, Z.-H.; Magiera, D.; Senanayake, C. H. Tetrahedron 2005, 61, 6386-6408.
18. Sasraku-Neequaye, L.; MacPherson, D.; Stockman, R. A. Tetrahedron Lett. 2006, 49, 1129-1132.
19. Qin, Y.; Wang, C.; Huang, Z.; Xia, X.; Jiang, Y. J. Org. Chem. 2004, 69, 8533-8536.
20. Herbrandson, H. E.; Dickerson, R. T. J. Am. Chem. Soc. 1959, 81, 4102-4106.
21. Jacobus, J.; Mislow, K. J. Am. Chem. Soc. 1967, 89, 5228-5234.
22. Mislow, K.; Simmons, T.; Melillo, J. T.; Ternay, Jr., A. L. J. Am. Chem. Soc. 1964, 86, 1452-1453.
23. Colonna, S.; Giovanni, R.; Montanari, F. Chem. Commun. 1968, 865-866.
24. Deyrup, J. A.; Moyer, C. L. J. Org. Chem. 1969, 34, 175-179.