Stereoselective synthesis of optically active substituted piperidines and pyrrolidines from amino acid derivatives by titanium(II)mediated intramolecular cyclization reaction

Tetrahedron Letters

Volumn 38, Issue 48, 1997, Pages 8351-8354

  Takayama, Yuuki ^a   Okamoto, Sentaro ^a   Sato, Fumie ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

PIPERIDINE DERIVATIVE; PYRROLIDINE DERIVATIVE; TITANIUM;

ARTICLE; CYCLIZATION; MOLECULAR DYNAMICS; MOLECULAR RECOGNITION; OUTCOMES RESEARCH; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0030703651     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10261-1     Document Type: Article

References (26)

1. Takayama, Y.; Gao, Y.; Sato, F. Angew. Chem., Int. Ed. Engl. 1997, 36, 851-853. Zirconium(II)-mediated intramolecular cyclization reaction of 2,7-or 2,8-bis-unsaturated ether has been reported: Knight, K. S.; Waymouth, R. M. Organometallics 1994, 13, 2575-2577. Takahashi, T.; Kondakov, D. Y.; Suzuki, N. Organometallics 1994, 13, 3411-3412. Bird, A. J.; Taylor, R. J. K.; Wei, X. Synlett 1995, 1237-1238.
2. Takayama, Y.; Gao, Y.; Sato, F. Angew. Chem., Int. Ed. Engl. 1997, 36, 851-853. Zirconium(II)-mediated intramolecular cyclization reaction of 2,7-or 2,8-bis-unsaturated ether has been reported: Knight, K. S.; Waymouth, R. M. Organometallics 1994, 13, 2575-2577. Takahashi, T.; Kondakov, D. Y.; Suzuki, N. Organometallics 1994, 13, 3411-3412. Bird, A. J.; Taylor, R. J. K.; Wei, X. Synlett 1995, 1237-1238.
3. Takayama, Y.; Gao, Y.; Sato, F. Angew. Chem., Int. Ed. Engl. 1997, 36, 851-853. Zirconium(II)-mediated intramolecular cyclization reaction of 2,7-or 2,8-bis-unsaturated ether has been reported: Knight, K. S.; Waymouth, R. M. Organometallics 1994, 13, 2575-2577. Takahashi, T.; Kondakov, D. Y.; Suzuki, N. Organometallics 1994, 13, 3411-3412. Bird, A. J.; Taylor, R. J. K.; Wei, X. Synlett 1995, 1237-1238.
4. Takayama, Y.; Gao, Y.; Sato, F. Angew. Chem., Int. Ed. Engl. 1997, 36, 851-853. Zirconium(II)-mediated intramolecular cyclization reaction of 2,7-or 2,8-bis-unsaturated ether has been reported: Knight, K. S.; Waymouth, R. M. Organometallics 1994, 13, 2575-2577. Takahashi, T.; Kondakov, D. Y.; Suzuki, N. Organometallics 1994, 13, 3411-3412. Bird, A. J.; Taylor, R. J. K.; Wei, X. Synlett 1995, 1237-1238.
5. Kasatkin, A.; Nakagawa, T.; Okamoto, S.; Sato, F. J. Am. Chem. Soc. 1995, 117 3881-3882. Harada, K.; Urabe, H.; Sato, F. Tetrahedron Lett. 1995, 36, 3203-3206. Takayanagi, Y.; Yamashita, K.; Yoshida, Y.; Sato, F. Chem. Commun. 1996, 1725-1726.
6. Kasatkin, A.; Nakagawa, T.; Okamoto, S.; Sato, F. J. Am. Chem. Soc. 1995, 117 3881-3882. Harada, K.; Urabe, H.; Sato, F. Tetrahedron Lett. 1995, 36, 3203-3206. Takayanagi, Y.; Yamashita, K.; Yoshida, Y.; Sato, F. Chem. Commun. 1996, 1725-1726.
7. Kasatkin, A.; Nakagawa, T.; Okamoto, S.; Sato, F. J. Am. Chem. Soc. 1995, 117 3881-3882. Harada, K.; Urabe, H.; Sato, F. Tetrahedron Lett. 1995, 36, 3203-3206. Takayanagi, Y.; Yamashita, K.; Yoshida, Y.; Sato, F. Chem. Commun. 1996, 1725-1726.
8. For recent review on synthesis of piperidines and pyrrolidines: Tisler, M.; Kolar, P. Adv. Heterocycl. Chem. 1995, 64, 1-79.
9. For the transition-metal-based routes to optically active piperidine and pyrrolidine compounds via the intramolecular carbon-carbon bond forming reaction, see the following most recent papers and references cited therein: (a) Sato, Y.; Saito, N.; Mori, M. Tetrahedron Lett. 1997, 38, 3931-3934.
10. (b) Laschat, S.; Fox, T. Synthesis 1997, 475-479.
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13. (e) Huwe, C. M.; Blechert, S. Synthesis 1997, 61-67.
14. (f) Barrett, A. G. M.; Baugh, S. P. D.; Gibson, V. C.; Giles, M. R.; Marshall, E. L.; Procopiou, P. A. Chem. Commun. 1997, 155-156.
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17. Southon, I. W.; Buckingham, J. Eds. Dictionary of Alkaloids; Chapman and Hall: London, 1989. Rubiralta, M.; Giralt, E.; Diez, A. Piperidine; Elsevier: Amsterdam, 1991.
18. Southon, I. W.; Buckingham, J. Eds. Dictionary of Alkaloids; Chapman and Hall: London, 1989. Rubiralta, M.; Giralt, E.; Diez, A. Piperidine; Elsevier: Amsterdam, 1991.
19. 3 = Et); 93%, 97.5%.
20. 3 = Et); 93%, 97.5%.
21. Reaction of 3 with 1 resulted in the intramolecular nucleophilic acyl substitution reaction providing optically active piperidines or pyrrolidines having 1-hydroxybicyclo[n.1.0]alkane or a conjugated enone moiety, respectively, see ref 3h.
22. 2O (0.21 mL) and NaF (0.3 g) were added. The resulting mixture was filtered through a pad of Celite and concentrated in vacuo. The residue was purified by column chromatography on silica gel (Wako C-200, hexane / AcOEt, 50 / 1) to give the pure main isomer 4 (40 mg, 75% yield) and a mixture of 4 and its diastereomer (9.4 mg, 18% yield).
23. Comins, D. L.; Joseph, S. P.; Hong, H.; Al-awar, R. S.; Foti, C. J.; Zhang, Y.; Chen, X.; LaMunyon, D. H.; Guerra-Weltzien, M. Pure Appl. Chem. 1997, 69, 477-481. Comins, D. L.; Al-awar, R. S. J. Org. Chem. 1995, 60, 711-716. Polniaszek, R. P.; Dillard, L. W. J. Org. Chem. 1992, 57, 4103-4110 and references cited therein.
24. Comins, D. L.; Joseph, S. P.; Hong, H.; Al-awar, R. S.; Foti, C. J.; Zhang, Y.; Chen, X.; LaMunyon, D. H.; Guerra-Weltzien, M. Pure Appl. Chem. 1997, 69, 477-481. Comins, D. L.; Al-awar, R. S. J. Org. Chem. 1995, 60, 711-716. Polniaszek, R. P.; Dillard, L. W. J. Org. Chem. 1992, 57, 4103-4110 and references cited therein.
25. Comins, D. L.; Joseph, S. P.; Hong, H.; Al-awar, R. S.; Foti, C. J.; Zhang, Y.; Chen, X.; LaMunyon, D. H.; Guerra-Weltzien, M. Pure Appl. Chem. 1997, 69, 477-481. Comins, D. L.; Al-awar, R. S. J. Org. Chem. 1995, 60, 711-716. Polniaszek, R. P.; Dillard, L. W. J. Org. Chem. 1992, 57, 4103-4110 and references cited therein.
26. The stereochemistry of the main product was determined by NOE-difference experiments. equation presented