Synthesis of enantiopure ethyl (1S,9aS)- and (1S,9aR)-1-phenyl-4,9-dioxohexahydropyrrolo[1,2-d][1,4]oxazepine-9a(7H)-carboxylate by carbenoid/ylide/Stevens-[1,2]-shift with ring enlargement

Tetrahedron Asymmetry

Volumn 11, Issue 16, 2000, Pages 3449-3453

  Chelucci, Giorgio ^a   Saba, Antonio ^a   Valenti, Raffaela ^a   Bacchi, Alessia ^b  

^a UNIVERSITY OF SASSARI   (Italy)

^b UNIVERSITY OF PARMA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

1 PHENYL 4,9 DIOXOHEXAHYDROPYRROLO]1,2 D][1,4]OXAZEPINE 9A CARBOXYLIC ACID ETHYL ESTER; OXAZEPINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; IN VITRO STUDY; INFRARED SPECTROPHOTOMETRY; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS; X RAY DIFFRACTION;

EID: 0034714136     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(00)00312-8     Document Type: Article

References (20)

1. Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; John Wiley & Sons: New York, 1997. West, F. G.; Naidu, B. N. J. Am. Chem. Soc. 1993, 115; 1177. Padwa, A.; Hornbuckle, S. F. Chem. Rev. 1991, 91, 263.
2. Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; John Wiley & Sons: New York, 1997. West, F. G.; Naidu, B. N. J. Am. Chem. Soc. 1993, 115; 1177. Padwa, A.; Hornbuckle, S. F. Chem. Rev. 1991, 91, 263.
3. Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; John Wiley & Sons: New York, 1997. West, F. G.; Naidu, B. N. J. Am. Chem. Soc. 1993, 115; 1177. Padwa, A.; Hornbuckle, S. F. Chem. Rev. 1991, 91, 263.
4. For a general review of the Stevens rearrangement, see Markò, I. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 3, pp 913-73.
5. Ollis, W. D.; Rey, M.; Sutherland, I. O. J. Chem. Soc., Perkin Trans. 1 1983, 1009.
6. West F.G., Naidu B.N. J. Am. Chem. Soc. 116:1994;8420.
7. Chelucci, G.; Saba, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 78. Chelucci, G.; Saba, A. Tetrahedron Lett. 1995, 36, 4673. Chelucci, G.; Saba, A.; Valle, G. Tetrahedron: Asymmetry 1995, 6, 807. Chelucci, G.; Saba, A. Tetrahedron: Asymmetry 1997, 8, 699. Chelucci, G.; Culeddu, N.; Saba, A.; Valenti, R. Tetrahedron Lett. 1999, 40, 8269.
8. Chelucci, G.; Saba, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 78. Chelucci, G.; Saba, A. Tetrahedron Lett. 1995, 36, 4673. Chelucci, G.; Saba, A.; Valle, G. Tetrahedron: Asymmetry 1995, 6, 807. Chelucci, G.; Saba, A. Tetrahedron: Asymmetry 1997, 8, 699. Chelucci, G.; Culeddu, N.; Saba, A.; Valenti, R. Tetrahedron Lett. 1999, 40, 8269.
9. Chelucci, G.; Saba, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 78. Chelucci, G.; Saba, A. Tetrahedron Lett. 1995, 36, 4673. Chelucci, G.; Saba, A.; Valle, G. Tetrahedron: Asymmetry 1995, 6, 807. Chelucci, G.; Saba, A. Tetrahedron: Asymmetry 1997, 8, 699. Chelucci, G.; Culeddu, N.; Saba, A.; Valenti, R. Tetrahedron Lett. 1999, 40, 8269.
10. Chelucci, G.; Saba, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 78. Chelucci, G.; Saba, A. Tetrahedron Lett. 1995, 36, 4673. Chelucci, G.; Saba, A.; Valle, G. Tetrahedron: Asymmetry 1995, 6, 807. Chelucci, G.; Saba, A. Tetrahedron: Asymmetry 1997, 8, 699. Chelucci, G.; Culeddu, N.; Saba, A.; Valenti, R. Tetrahedron Lett. 1999, 40, 8269.
11. Chelucci, G.; Saba, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 78. Chelucci, G.; Saba, A. Tetrahedron Lett. 1995, 36, 4673. Chelucci, G.; Saba, A.; Valle, G. Tetrahedron: Asymmetry 1995, 6, 807. Chelucci, G.; Saba, A. Tetrahedron: Asymmetry 1997, 8, 699. Chelucci, G.; Culeddu, N.; Saba, A.; Valenti, R. Tetrahedron Lett. 1999, 40, 8269.
12. For a similar reaction affording a 6,6-system, see: Zaragoza, F. Synlett 1995, 237.
13. Anslow, A. S.; Harwood, L. M.; Phillips, H.; Watkin, D. Tetrahedron: Asymmetry 1991, 2, 169. Harwood, L. M.; Macro, J.; Watkin, D.; Williams, E.; Wong, L. F. Tetrahedron: Asymmetry 1992, 3, 1127. Alker, D; Harwood, L. M.; Williams, E. Tetrahedron Lett. 1998, 39, 475.
14. Anslow, A. S.; Harwood, L. M.; Phillips, H.; Watkin, D. Tetrahedron: Asymmetry 1991, 2, 169. Harwood, L. M.; Macro, J.; Watkin, D.; Williams, E.; Wong, L. F. Tetrahedron: Asymmetry 1992, 3, 1127. Alker, D; Harwood, L. M.; Williams, E. Tetrahedron Lett. 1998, 39, 475.
15. Anslow, A. S.; Harwood, L. M.; Phillips, H.; Watkin, D. Tetrahedron: Asymmetry 1991, 2, 169. Harwood, L. M.; Macro, J.; Watkin, D.; Williams, E.; Wong, L. F. Tetrahedron: Asymmetry 1992, 3, 1127. Alker, D; Harwood, L. M.; Williams, E. Tetrahedron Lett. 1998, 39, 475.
16. Dellaria J.F. Jr., Santarsiero B.D. J. Org. Chem. 54:1989;3916.
17. Scott Beall L., Padwa A. Tetrahedron Lett. 39:1998;4159.
18. Zibuck R., Streiber J.M. J. Org. Chem. 54:1989;4717.
19. West, F. G.; Naidu, B. N.; Tester, R. W. J. Org. Chem. 1994, 59, 6892. Clark, J. S.; Krowiak, S. A.; Street, L. J. Tetrahedron Lett. 1993, 34, 4385.
20. West, F. G.; Naidu, B. N.; Tester, R. W. J. Org. Chem. 1994, 59, 6892. Clark, J. S.; Krowiak, S. A.; Street, L. J. Tetrahedron Lett. 1993, 34, 4385.