Stereoselective synthesis of L-733,060

Tetrahedron Letters

Volumn 44, Issue 5, 2003, Pages 915-917

  Bhaskar, G ^a   Rao, B Venkateswara ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

3 [3,5 BIS(TRIFLUOROMETHYL)BENZYLOXY] 2 PHENYLPIPERIDINE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0037467858     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02772-7     Document Type: Article

References (25)

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13. 3)).
14. For recent reviews on metathesis, see: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450; (b) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371-388; (c) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012-3043.
15. For recent reviews on metathesis, see: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450; (b) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371-388; (c) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012-3043.
16. For recent reviews on metathesis, see: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450; (b) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371-388; (c) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012-3043.
17. For syntheses of piperidine moieties using ring-closing metathesis, see: (a) Pernerstorfer, J.; Schuster, M.; Blechert, S. Synthesis 1999, 138-144; (b) Zumpe, F. L.; Kazmaier, U. Synthesis 1999, 1785-1791; (c) Felpin, F.; Girard, S.; Vo-Thanh, G.; Robins, R. J.; Villieras, J.; Lebreton, J. J. Org. Chem. 2001, 66, 6305-6312; (d) Banba, Y.; Abe, C.; Nemoto, H.; Kato, A.; Adachi, I.; Takahata, H. Tetrahedron: Asymmetry 2001, 12, 817-819; (e) Cossy, J.; Willis, C.; Bellosta, V.; BouzBouz, S. J. Org. Chem. 2002, 67, 1982-1992; (f) Ginesta, X.; Pericas, M. A.; Riera, A. Tetrahedron Lett. 2002, 43, 779-782; (g) Davies, S. G.; Iwamoto, K.; Smethurst, C. A. P.; Smith, A. D.; Rodriguez-Solla, H. Synlett 2002, 1146-1148.
18. For syntheses of piperidine moieties using ring-closing metathesis, see: (a) Pernerstorfer, J.; Schuster, M.; Blechert, S. Synthesis 1999, 138-144; (b) Zumpe, F. L.; Kazmaier, U. Synthesis 1999, 1785-1791; (c) Felpin, F.; Girard, S.; Vo-Thanh, G.; Robins, R. J.; Villieras, J.; Lebreton, J. J. Org. Chem. 2001, 66, 6305-6312; (d) Banba, Y.; Abe, C.; Nemoto, H.; Kato, A.; Adachi, I.; Takahata, H. Tetrahedron: Asymmetry 2001, 12, 817-819; (e) Cossy, J.; Willis, C.; Bellosta, V.; BouzBouz, S. J. Org. Chem. 2002, 67, 1982-1992; (f) Ginesta, X.; Pericas, M. A.; Riera, A. Tetrahedron Lett. 2002, 43, 779-782; (g) Davies, S. G.; Iwamoto, K.; Smethurst, C. A. P.; Smith, A. D.; Rodriguez-Solla, H. Synlett 2002, 1146-1148.
19. For syntheses of piperidine moieties using ring-closing metathesis, see: (a) Pernerstorfer, J.; Schuster, M.; Blechert, S. Synthesis 1999, 138-144; (b) Zumpe, F. L.; Kazmaier, U. Synthesis 1999, 1785-1791; (c) Felpin, F.; Girard, S.; Vo-Thanh, G.; Robins, R. J.; Villieras, J.; Lebreton, J. J. Org. Chem. 2001, 66, 6305-6312; (d) Banba, Y.; Abe, C.; Nemoto, H.; Kato, A.; Adachi, I.; Takahata, H. Tetrahedron: Asymmetry 2001, 12, 817-819; (e) Cossy, J.; Willis, C.; Bellosta, V.; BouzBouz, S. J. Org. Chem. 2002, 67, 1982-1992; (f) Ginesta, X.; Pericas, M. A.; Riera, A. Tetrahedron Lett. 2002, 43, 779-782; (g) Davies, S. G.; Iwamoto, K.; Smethurst, C. A. P.; Smith, A. D.; Rodriguez-Solla, H. Synlett 2002, 1146-1148.
20. For syntheses of piperidine moieties using ring-closing metathesis, see: (a) Pernerstorfer, J.; Schuster, M.; Blechert, S. Synthesis 1999, 138-144; (b) Zumpe, F. L.; Kazmaier, U. Synthesis 1999, 1785-1791; (c) Felpin, F.; Girard, S.; Vo-Thanh, G.; Robins, R. J.; Villieras, J.; Lebreton, J. J. Org. Chem. 2001, 66, 6305-6312; (d) Banba, Y.; Abe, C.; Nemoto, H.; Kato, A.; Adachi, I.; Takahata, H. Tetrahedron: Asymmetry 2001, 12, 817-819; (e) Cossy, J.; Willis, C.; Bellosta, V.; BouzBouz, S. J. Org. Chem. 2002, 67, 1982-1992; (f) Ginesta, X.; Pericas, M. A.; Riera, A. Tetrahedron Lett. 2002, 43, 779-782; (g) Davies, S. G.; Iwamoto, K.; Smethurst, C. A. P.; Smith, A. D.; Rodriguez-Solla, H. Synlett 2002, 1146-1148.
21. For syntheses of piperidine moieties using ring-closing metathesis, see: (a) Pernerstorfer, J.; Schuster, M.; Blechert, S. Synthesis 1999, 138-144; (b) Zumpe, F. L.; Kazmaier, U. Synthesis 1999, 1785-1791; (c) Felpin, F.; Girard, S.; Vo-Thanh, G.; Robins, R. J.; Villieras, J.; Lebreton, J. J. Org. Chem. 2001, 66, 6305-6312; (d) Banba, Y.; Abe, C.; Nemoto, H.; Kato, A.; Adachi, I.; Takahata, H. Tetrahedron: Asymmetry 2001, 12, 817-819; (e) Cossy, J.; Willis, C.; Bellosta, V.; BouzBouz, S. J. Org. Chem. 2002, 67, 1982-1992; (f) Ginesta, X.; Pericas, M. A.; Riera, A. Tetrahedron Lett. 2002, 43, 779-782; (g) Davies, S. G.; Iwamoto, K.; Smethurst, C. A. P.; Smith, A. D.; Rodriguez-Solla, H. Synlett 2002, 1146-1148.
22. For syntheses of piperidine moieties using ring-closing metathesis, see: (a) Pernerstorfer, J.; Schuster, M.; Blechert, S. Synthesis 1999, 138-144; (b) Zumpe, F. L.; Kazmaier, U. Synthesis 1999, 1785-1791; (c) Felpin, F.; Girard, S.; Vo-Thanh, G.; Robins, R. J.; Villieras, J.; Lebreton, J. J. Org. Chem. 2001, 66, 6305-6312; (d) Banba, Y.; Abe, C.; Nemoto, H.; Kato, A.; Adachi, I.; Takahata, H. Tetrahedron: Asymmetry 2001, 12, 817-819; (e) Cossy, J.; Willis, C.; Bellosta, V.; BouzBouz, S. J. Org. Chem. 2002, 67, 1982-1992; (f) Ginesta, X.; Pericas, M. A.; Riera, A. Tetrahedron Lett. 2002, 43, 779-782; (g) Davies, S. G.; Iwamoto, K.; Smethurst, C. A. P.; Smith, A. D.; Rodriguez-Solla, H. Synlett 2002, 1146-1148.
23. For syntheses of piperidine moieties using ring-closing metathesis, see: (a) Pernerstorfer, J.; Schuster, M.; Blechert, S. Synthesis 1999, 138-144; (b) Zumpe, F. L.; Kazmaier, U. Synthesis 1999, 1785-1791; (c) Felpin, F.; Girard, S.; Vo-Thanh, G.; Robins, R. J.; Villieras, J.; Lebreton, J. J. Org. Chem. 2001, 66, 6305-6312; (d) Banba, Y.; Abe, C.; Nemoto, H.; Kato, A.; Adachi, I.; Takahata, H. Tetrahedron: Asymmetry 2001, 12, 817-819; (e) Cossy, J.; Willis, C.; Bellosta, V.; BouzBouz, S. J. Org. Chem. 2002, 67, 1982-1992; (f) Ginesta, X.; Pericas, M. A.; Riera, A. Tetrahedron Lett. 2002, 43, 779-782; (g) Davies, S. G.; Iwamoto, K.; Smethurst, C. A. P.; Smith, A. D.; Rodriguez-Solla, H. Synlett 2002, 1146-1148.
24. Tomooka, K.; Nakazaki, A.; Nakai, T. J. Am. Chem. Soc. 2000, 122, 408-409, see supporting information.
25. 3): δ 20.25, 28.27, 46.86, 64.06, 69.96, 77.40, 121.12 (m), 123.22 (q, J=272.6 Hz), 126.72, 127.16, 127.37, 128.11, 131.26 (q, J=33.3), 141.11, 141.41; FAB-MS m/z: 404 (M+1), 227, 176, 160.