Asymmetric synthesis of functionalized aza-cyclic amino acids with quaternary stereocenters by a phase-transfer-catalyzed alkylation strategy

Organic Letters

Volumn 7, Issue 2, 2005, Pages 191-193

  Ooi, Takashi ^a   Miki, Takashi ^a   Maruoka, Keiji ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; AMMONIUM DERIVATIVE; BROMINE DERIVATIVE; CARBON; CARBONYL DERIVATIVE;

ALKYLATION; ARTICLE; CATALYST; CHEMICAL PROCEDURES; CHEMICAL REACTION; REDUCTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 13444267639     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol047921p     Document Type: Article

References (25)

1. For example, see: (a) Ward, P.; Ewan, G. B.; Jordan, C. C.; Ireland, S. J.; Hagan, R. M.; Brown, J. R. J. Med. Chem. 1990, 33, 1848. (b) Bisang, C.; Weber, C.; Inglis, J.; Schiffer, C. A.; van Gunsteren, W. F.; Jelesarov, I.; Bosshard, H. R.; Robinson, J. A. J. Am. Chem. Soc. 1995, 117, 7904.
2. For example, see: (a) Ward, P.; Ewan, G. B.; Jordan, C. C.; Ireland, S. J.; Hagan, R. M.; Brown, J. R. J. Med. Chem. 1990, 33, 1848. (b) Bisang, C.; Weber, C.; Inglis, J.; Schiffer, C. A.; van Gunsteren, W. F.; Jelesarov, I.; Bosshard, H. R.; Robinson, J. A. J. Am. Chem. Soc. 1995, 117, 7904.
3. (a) Long, R. D.; Moeller, K. D. J. Am. Chem. Soc. 1997, 119, 12394.
4. (b) Trancard, D.; Tout, J.-B.; Giard, T.; Chichaoui, I.; Cahard, D.; Plaquevent, J.-C. Tetrahedron Lett. 2000, 41, 3843.
5. (c) Gutiérrez-Rodríguez, M.; García-López, M. T.; Herranz, R. Tetrahedron 2004, 60, 5177.
6. (a) Vignola, N.; List, B. J. Am. Chem. Soc. 2004, 126, 450.
7. (b) Halland, N.; Braunton, A.; Bachmann, S.; Marigo, M.; Jørgensen, K. A. J. Am. Chem. Soc. 2004, 126, 4790.
8. For a comprehensive review, see: Cativiela, C.; Díaz-de-Villegas, M. D. Tetrahedron: Asymmetry 2000, 11, 645 and valuable sets of references therein.
9. Recent representative examples: (a) Glaeske, K. W.; West, F. G. Org. Lett. 1999, 1, 31. (b) Abellán, T.; Mancheño, B.; Nájera, C.; Sansano, J. M. Tetrahedron 2001, 57, 6627. (c) Gil, A. M.; Buñuel, E.; Díaz-de-Villegas, M. D.; Cativiela, C. Tetrahedron: Asymmetry 2003, 14, 1479. (d) Tamura, O.; Yanagimachi, T.; Ishibashi, H. Tetrahedron: Asymmetry 2003, 14, 3033. (e) Le Nguyen, B. K.; Langlois, N. Tetrahedron Lett. 2003, 44, 5961. (f) Andrei, M.; Efskind, J.; Viljugrein, T.; Römming, C.; Undheim, K. Tetrahedron: Asymmetry 2004, 15, 1301. (g) Bashiardes, G.; Safir, I.; Barbot, F.; Laduranty, J. Tetrahedron Lett. 2004, 45, 1567. (h) Khasanov, A. B.; Ramirez-Weinhouse, M. M.; Webb, T. R.; Thiruvazhi, M. J. Org. Chem. 2004, 69, 5766.
10. Recent representative examples: (a) Glaeske, K. W.; West, F. G. Org. Lett. 1999, 1, 31. (b) Abellán, T.; Mancheño, B.; Nájera, C.; Sansano, J. M. Tetrahedron 2001, 57, 6627. (c) Gil, A. M.; Buñuel, E.; Díaz-de-Villegas, M. D.; Cativiela, C. Tetrahedron: Asymmetry 2003, 14, 1479. (d) Tamura, O.; Yanagimachi, T.; Ishibashi, H. Tetrahedron: Asymmetry 2003, 14, 3033. (e) Le Nguyen, B. K.; Langlois, N. Tetrahedron Lett. 2003, 44, 5961. (f) Andrei, M.; Efskind, J.; Viljugrein, T.; Römming, C.; Undheim, K. Tetrahedron: Asymmetry 2004, 15, 1301. (g) Bashiardes, G.; Safir, I.; Barbot, F.; Laduranty, J. Tetrahedron Lett. 2004, 45, 1567. (h) Khasanov, A. B.; Ramirez-Weinhouse, M. M.; Webb, T. R.; Thiruvazhi, M. J. Org. Chem. 2004, 69, 5766.
11. Recent representative examples: (a) Glaeske, K. W.; West, F. G. Org. Lett. 1999, 1, 31. (b) Abellán, T.; Mancheño, B.; Nájera, C.; Sansano, J. M. Tetrahedron 2001, 57, 6627. (c) Gil, A. M.; Buñuel, E.; Díaz-de-Villegas, M. D.; Cativiela, C. Tetrahedron: Asymmetry 2003, 14, 1479. (d) Tamura, O.; Yanagimachi, T.; Ishibashi, H. Tetrahedron: Asymmetry 2003, 14, 3033. (e) Le Nguyen, B. K.; Langlois, N. Tetrahedron Lett. 2003, 44, 5961. (f) Andrei, M.; Efskind, J.; Viljugrein, T.; Römming, C.; Undheim, K. Tetrahedron: Asymmetry 2004, 15, 1301. (g) Bashiardes, G.; Safir, I.; Barbot, F.; Laduranty, J. Tetrahedron Lett. 2004, 45, 1567. (h) Khasanov, A. B.; Ramirez-Weinhouse, M. M.; Webb, T. R.; Thiruvazhi, M. J. Org. Chem. 2004, 69, 5766.
12. Recent representative examples: (a) Glaeske, K. W.; West, F. G. Org. Lett. 1999, 1, 31. (b) Abellán, T.; Mancheño, B.; Nájera, C.; Sansano, J. M. Tetrahedron 2001, 57, 6627. (c) Gil, A. M.; Buñuel, E.; Díaz-de-Villegas, M. D.; Cativiela, C. Tetrahedron: Asymmetry 2003, 14, 1479. (d) Tamura, O.; Yanagimachi, T.; Ishibashi, H. Tetrahedron: Asymmetry 2003, 14, 3033. (e) Le Nguyen, B. K.; Langlois, N. Tetrahedron Lett. 2003, 44, 5961. (f) Andrei, M.; Efskind, J.; Viljugrein, T.; Römming, C.; Undheim, K. Tetrahedron: Asymmetry 2004, 15, 1301. (g) Bashiardes, G.; Safir, I.; Barbot, F.; Laduranty, J. Tetrahedron Lett. 2004, 45, 1567. (h) Khasanov, A. B.; Ramirez-Weinhouse, M. M.; Webb, T. R.; Thiruvazhi, M. J. Org. Chem. 2004, 69, 5766.
13. Recent representative examples: (a) Glaeske, K. W.; West, F. G. Org. Lett. 1999, 1, 31. (b) Abellán, T.; Mancheño, B.; Nájera, C.; Sansano, J. M. Tetrahedron 2001, 57, 6627. (c) Gil, A. M.; Buñuel, E.; Díaz-de-Villegas, M. D.; Cativiela, C. Tetrahedron: Asymmetry 2003, 14, 1479. (d) Tamura, O.; Yanagimachi, T.; Ishibashi, H. Tetrahedron: Asymmetry 2003, 14, 3033. (e) Le Nguyen, B. K.; Langlois, N. Tetrahedron Lett. 2003, 44, 5961. (f) Andrei, M.; Efskind, J.; Viljugrein, T.; Römming, C.; Undheim, K. Tetrahedron: Asymmetry 2004, 15, 1301. (g) Bashiardes, G.; Safir, I.; Barbot, F.; Laduranty, J. Tetrahedron Lett. 2004, 45, 1567. (h) Khasanov, A. B.; Ramirez-Weinhouse, M. M.; Webb, T. R.; Thiruvazhi, M. J. Org. Chem. 2004, 69, 5766.
14. Recent representative examples: (a) Glaeske, K. W.; West, F. G. Org. Lett. 1999, 1, 31. (b) Abellán, T.; Mancheño, B.; Nájera, C.; Sansano, J. M. Tetrahedron 2001, 57, 6627. (c) Gil, A. M.; Buñuel, E.; Díaz-de-Villegas, M. D.; Cativiela, C. Tetrahedron: Asymmetry 2003, 14, 1479. (d) Tamura, O.; Yanagimachi, T.; Ishibashi, H. Tetrahedron: Asymmetry 2003, 14, 3033. (e) Le Nguyen, B. K.; Langlois, N. Tetrahedron Lett. 2003, 44, 5961. (f) Andrei, M.; Efskind, J.; Viljugrein, T.; Römming, C.; Undheim, K. Tetrahedron: Asymmetry 2004, 15, 1301. (g) Bashiardes, G.; Safir, I.; Barbot, F.; Laduranty, J. Tetrahedron Lett. 2004, 45, 1567. (h) Khasanov, A. B.; Ramirez-Weinhouse, M. M.; Webb, T. R.; Thiruvazhi, M. J. Org. Chem. 2004, 69, 5766.
15. Recent representative examples: (a) Glaeske, K. W.; West, F. G. Org. Lett. 1999, 1, 31. (b) Abellán, T.; Mancheño, B.; Nájera, C.; Sansano, J. M. Tetrahedron 2001, 57, 6627. (c) Gil, A. M.; Buñuel, E.; Díaz-de-Villegas, M. D.; Cativiela, C. Tetrahedron: Asymmetry 2003, 14, 1479. (d) Tamura, O.; Yanagimachi, T.; Ishibashi, H. Tetrahedron: Asymmetry 2003, 14, 3033. (e) Le Nguyen, B. K.; Langlois, N. Tetrahedron Lett. 2003, 44, 5961. (f) Andrei, M.; Efskind, J.; Viljugrein, T.; Römming, C.; Undheim, K. Tetrahedron: Asymmetry 2004, 15, 1301. (g) Bashiardes, G.; Safir, I.; Barbot, F.; Laduranty, J. Tetrahedron Lett. 2004, 45, 1567. (h) Khasanov, A. B.; Ramirez-Weinhouse, M. M.; Webb, T. R.; Thiruvazhi, M. J. Org. Chem. 2004, 69, 5766.
16. Recent representative examples: (a) Glaeske, K. W.; West, F. G. Org. Lett. 1999, 1, 31. (b) Abellán, T.; Mancheño, B.; Nájera, C.; Sansano, J. M. Tetrahedron 2001, 57, 6627. (c) Gil, A. M.; Buñuel, E.; Díaz-de-Villegas, M. D.; Cativiela, C. Tetrahedron: Asymmetry 2003, 14, 1479. (d) Tamura, O.; Yanagimachi, T.; Ishibashi, H. Tetrahedron: Asymmetry 2003, 14, 3033. (e) Le Nguyen, B. K.; Langlois, N. Tetrahedron Lett. 2003, 44, 5961. (f) Andrei, M.; Efskind, J.; Viljugrein, T.; Römming, C.; Undheim, K. Tetrahedron: Asymmetry 2004, 15, 1301. (g) Bashiardes, G.; Safir, I.; Barbot, F.; Laduranty, J. Tetrahedron Lett. 2004, 45, 1567. (h) Khasanov, A. B.; Ramirez-Weinhouse, M. M.; Webb, T. R.; Thiruvazhi, M. J. Org. Chem. 2004, 69, 5766.
17. For rare examples involving catalytic asymmetric bond formation, see: (a) multistep synthesis via Sharpless epoxidation: Brennan, C. J.; Pattenden, G.; Rescourio, G. Tetrahedron Lett. 2003, 44, 8757. (b) based on phase-transfer-catalyzed alkylation of α-amino acid Schiff base (enantiomeric excess was not determined): Belokon, Y. N.; Bhave, D.; D'Addario, D.; Groaz, E.; North, M.; Tagliazucca, V. Tetrahedron 2004, 60, 1849.
18. For rare examples involving catalytic asymmetric bond formation, see: (a) multistep synthesis via Sharpless epoxidation: Brennan, C. J.; Pattenden, G.; Rescourio, G. Tetrahedron Lett. 2003, 44, 8757. (b) based on phase-transfer-catalyzed alkylation of α-amino acid Schiff base (enantiomeric excess was not determined): Belokon, Y. N.; Bhave, D.; D'Addario, D.; Groaz, E.; North, M.; Tagliazucca, V. Tetrahedron 2004, 60, 1849.
19. (a) Kawabata, T.; Kawakami, S.; Majumdar, S. J. Am. Chem. Soc. 2003, 125, 13012.
20. See also: (b) Brewster, A. G.; Jayatissa, J.; Mitchell, M. B.; Schofield, A.; Stoodley, R. J. Tetrahedron Lett. 2002, 43, 3919.
21. (a) Ooi, T.; Miki, T.; Taniguchi, M.; Shiraishi, M.; Takeuchi, M.; Maruoka, K. Angew. Chem., Int. Ed. 2003, 42, 3796.
22. See also: (b) Ooi, T.; Doda, K.; Maruoka, K. Org. Lett. 2001, 3, 1273. (c) Ooi, T.; Taniguchi, M.; Kameda, M.; Maruoka, K. Angew. Chem., Int. Ed. 2002, 41, 4542.
23. See also: (b) Ooi, T.; Doda, K.; Maruoka, K. Org. Lett. 2001, 3, 1273. (c) Ooi, T.; Taniguchi, M.; Kameda, M.; Maruoka, K. Angew. Chem., Int. Ed. 2002, 41, 4542.
24. (a) Van Emelen, K.; De Wit, T.; Hoornaert, G. J.; Compernolle, F. Org. Lett. 2000, 2, 3083.
25. (b) Van Emelen, K.; De Wit, T.; Hoornaert, G. J.; Compernolle, F. Tetrahedron 2002, 58, 4225.