Practical methods for the preparation of spiro[benzo[c]thiophene- 1(3H),4'-piperidine]-(2S)-oxide by resolution and asymmetric sulfoxidation

Tetrahedron Asymmetry

Volumn 9, Issue 15, 1998, Pages 2567-2570

  Nishi, Takahide ^a   Nakajima, Katsuyoshi ^a   Iio, Yukiko ^a   Ishibashi, Koki ^a   Fukazawa, Tetsuya ^a  

^a DAIICHI SANKYO CO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

PIPERIDINE DERIVATIVE; SPIRO[BENZO[C]THIOPHENE 1(3H),4' PIPERIDINE]OXIDE; TACHYKININ RECEPTOR ANTAGONIST; THIOPHENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; OXIDATION REDUCTION REACTION; PRIORITY JOURNAL;

EID: 0032493831     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00257-2     Document Type: Article

References (28)

1. (a) Carreño, M. C. Chem. Rev. 1995, 95, 1717-1760.
2. (b) Kagan, H. B. In Catalytic Asymmetric Synthesis, Ojima, I. Ed; VCH: New York, 1993; Chapter 4.3, pp. 203-226.
3. (c) Anderson, K. K. In The Chemistry of Sulfones and Sulfoxides, Patai, S., Rappoport, Z., Stirling, C. J. M., Eds; John Wiley and Sons: Chichester, England, 1988; Chapter 16, pp. 823-849 and references cited therein.
4. (a) Nishi, T.; Fukazawa, T.; Kurata, H.; Ishibashi, K.; Nakajima, K.; Yamaguchi, T.; Ito, K. EP-776893-A1 (1996), Sankyo Co., Ltd.
5. (b) Kubota, H.; Kakefuda, A.; Nagaoka, H.; Yamamoto, O.; Ikeda, K.; Takeuchi, M.; Shibanuma, T.; Isomura, Y. Chem. Pharm. Bull. 1998, 46, 242-254.
6. Parham, W. E.; Egberg, D. C.; Sayed, Y. A.; Thraikill, R. W.; Keyser, G. E.; Neu, M.; Montgomery, W. C.; Jones, L. D. J. Org. Chem. 1976, 41, 2628-2633.
7. All new compounds are fully characterized by their spectroscopic and analytical data.
8. 3, R=0.066. Full X-ray crystallographic data will be deposited with the Cambridge Crystallographic Data Centre.
9. (a) Bendazzoli, P.; Di Furia, F.; Licini, G.; Modena, G. Tetrahedron Lett. 1993, 34, 2975-2978.
10. (b) Kagan, H. B.; Rebier, F. Synlett. 1990, 643-650 and references cited therein.
11. (a) Colonna, S.; Gaggero, N.; Casella, L.; Carrea, G.; Pasta, P. Tetrahedron: Asymmetry 1992, 3, 95-106.
12. (b) Fu, H.; Kondo, H.; Ichikawa, Y.; Look, G. C.; Wong, C.-H. J. Org. Chem. 1992, 57, 7265-7270.
13. (c) Madesclaire, M.; Fauve, A.; Metin, J.; Carpy, A. Tetrahedron: Asymmetry 1990, 1, 311-314.
14. (a) Superchi, S.; Rosini, C. Tetrahedron: Asymmetry 1997, 8, 349-352.
15. (b) Brunel, J.-M.; Kagan, H. B. Bull. Soc. Chim. Fr. 1996, 133, 1109-1115.
16. (c) Di Furia, F.; Licini, G.; Modena, G.; Motterle, R.; Nugent, W. A. J. Org. Chem. 1996, 61, 5175-5177.
17. (d) Komatsu, N.; Hashizume, M.; Sugita, T.; Uemura, S. J. Org. Chem. 1993, 58, 4529-4533.
18. (e) Sasaki, C.; Nakajima, K.; Kojima, M.; Fujita, J. J. Bull. Chem. Soc. Jpn 1991, 64, 1318-1324.
19. (f) Beckwith, A. L. J.; Boate, D. R. J. Chem. Soc., Chem. Commun. 1986, 189-190.
20. (a) Halterman, R. L.; Jan, S.-T.; Nimmons, H. L.; Standlee, D. J.; Khan, M. A. Tetrahedron 1997, 53, 11257-11276.
21. (b) Nagata, T.; Imagawa, K.; Yamada, T.; Mukaiyama, T. Bull. Chem. Soc. Jpn 1995, 68, 3241-3246.
22. (c) Noda, K.; Hosoya, N.; Irie, R.; Yamashita, Y.; Katsuki, T. Tetrahedron 1994, 50, 9609-9618.
23. (d) Palucki, M.; Hanson, P.; Jacobsen, E. N. Tetrahedron Lett. 1992, 33, 7111-7114.
24. (a) Vetter, A. H.; Berkessel, A. Tetrahedron Lett. 1998, 39, 1741-1744.
25. (b) Bolm, C.; Bienewald, F. Angew. Chem. Int. Ed. Engl. 1995. 34, 2640-2642.
26. (c) Nakajima, K.; Kojima, M.; Toriumi, K.; Saito, K.; Fujita, J. Bull. Chem. Soc. Jpn 1989, 62, 760-767.
27. (a) Davis, F. A.; Kumar, A.; Chen, B.-C. J. Org. Chem. 1991, 56, 1143-1145.
28. (b) Davis, F. A.; Reddy, R. T.; Han, W.; Carroll, P. J. J. Am. Chem. Soc. 1992, 114, 1428-1437.