Asymmetric synthesis of enantiomerically pure spiro [((2S)- hydroxy)indane-1,4'-piperidine]

Tetrahedron Asymmetry

Volumn 10, Issue 9, 1999, Pages 1787-1793

  Takemoto, Toshiyasu ^a   Nakajima, Katsuyoshi ^a   Iio, Yukiko ^a   Tamura, Masakazu ^a   Nishi, Takahide ^a  

^a DAIICHI SANKYO CO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

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

ARTICLE; CONFORMATIONAL TRANSITION; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; ENANTIOMER; PRIORITY JOURNAL; STRUCTURE ANALYSIS;

EID: 0033532263     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00172-X     Document Type: Article

References (16)

1. Tata, J. R.; Nargund, R. P.; Murphy, M. M.; Johnston, D. B. R.; Patchett, A. A.; Cheng, K.; Wei, L.; Chan, W. W.-S.; Butler, B.; Jacks, T. M.; Hickey, G.; Smith, R. Bioorg. Med. Chem. Lett. 1997, 7, 663-668.
2. Unpublished studies.
3. Nishi, T.; Fukazawa, T.; Ishibashi, K.; Nakajima, K.; Sugioka, Y.; Iio, Y.; Kurata, H.; Itoh, K.; Mukaiyama, O.; Satoh, Y.; Yamaguchi, T. Bioorg. Med. Chem. Lett. 1999, 9, 875-880. Synthesis: Nishi, T.; Nakajima, K.; Iio, Y.; Ishibashi, K.; Fukazawa, T. Tetrahedron: Asymmetry 1998, 9, 2567-2570.
4. Nishi, T.; Fukazawa, T.; Ishibashi, K.; Nakajima, K.; Sugioka, Y.; Iio, Y.; Kurata, H.; Itoh, K.; Mukaiyama, O.; Satoh, Y.; Yamaguchi, T. Bioorg. Med. Chem. Lett. 1999, 9, 875-880. Synthesis: Nishi, T.; Nakajima, K.; Iio, Y.; Ishibashi, K.; Fukazawa, T. Tetrahedron: Asymmetry 1998, 9, 2567-2570.
5. Chambers, M. S.; Baker, R.; Billington, D. C.; Knight, A. K.; Middlemiss, D. N.; Wong, E. H. F. J. Med. Chem. 1992, 35, 2033-2039.
6. Rudolph, J.; Reddy, K. L.; Chiang, J. P.; Sharpless, K. B. J. Am. Chem. Soc. 1997, 119, 6189-6190.
7. Varghese, J. P.; Sudalai, A.; Iyer, S. Synth. Commun. 1995, 25, 2267-2273.
8. (a) Corey, E. J.; Bakshi, R. K.; Shibata, S. J. Am. Chem. Soc. 1987, 109, 5551-5553.
9. (b) Corey, E. J.; Bakshi, R. K.; Shibata, S.; Chen, C.-P.; Singh, V. K. J. Am. Chem. Soc. 1987, 109, 7925-7926. The asymmetric reduction using chirally modified borohydride as a catalyst has been in use since 1981 (Hirao, A.; Itsuno, S.; Nakahama, S.; Yamazaki, N. J. Chem. Soc., Chem. Commun. 1981, 315-317). For a review on asymmetric boron-catalyzed reactions, see: Deloux, L.; Srebnik, M. Chem. Rev. 1993, 93, 763-784.
10. (b) Corey, E. J.; Bakshi, R. K.; Shibata, S.; Chen, C.-P.; Singh, V. K. J. Am. Chem. Soc. 1987, 109, 7925-7926. The asymmetric reduction using chirally modified borohydride as a catalyst has been in use since 1981 (Hirao, A.; Itsuno, S.; Nakahama, S.; Yamazaki, N. J. Chem. Soc., Chem. Commun. 1981, 315-317). For a review on asymmetric boron-catalyzed reactions, see: Deloux, L.; Srebnik, M. Chem. Rev. 1993, 93, 763-784.
11. (b) Corey, E. J.; Bakshi, R. K.; Shibata, S.; Chen, C.-P.; Singh, V. K. J. Am. Chem. Soc. 1987, 109, 7925-7926. The asymmetric reduction using chirally modified borohydride as a catalyst has been in use since 1981 (Hirao, A.; Itsuno, S.; Nakahama, S.; Yamazaki, N. J. Chem. Soc., Chem. Commun. 1981, 315-317). For a review on asymmetric boron-catalyzed reactions, see: Deloux, L.; Srebnik, M. Chem. Rev. 1993, 93, 763-784.
12. 3, R=0.065. Full X-ray crystallographic data will be deposited with the Cambridge Crystallographic Data Centre.
13. (a) Palucki, M.; McCormik, G. J.; Jacobsen, E. N. Tetrahedron Lett. 1995, 36, 5457-5460.
14. (b) Jacobsen, E. N.; Zhang, W.; Muci, A. R.; Ecker, J. R.; Deng, L. J. Am. Chem. Soc. 1991, 113, 7063-7064.
15. (c) Zhang, W.; Jacobsen, E. N. J. Org. Chem. 1991, 56, 2296-2298. For a review on recent progress in asymmetric epoxidation, see: Jacobsen, E. N. In Catalytic Asymmetric Synthesis; Ojima, I., Ed; VCH: New York, 1993; Chapter 4.2, pp. 159-202 and references cited therein.
16. (c) Zhang, W.; Jacobsen, E. N. J. Org. Chem. 1991, 56, 2296-2298. For a review on recent progress in asymmetric epoxidation, see: Jacobsen, E. N. In Catalytic Asymmetric Synthesis; Ojima, I., Ed; VCH: New York, 1993; Chapter 4.2, pp. 159-202 and references cited therein.