Selective synthesis of either enantiomer of α-amino acids by switching the regiochemistry of the tricyclic iminolactones prepared from a single chiral source

Journal of Organic Chemistry

Volumn 68, Issue 2, 2003, Pages 658-661

  Xu, Peng Fei ^b   Lu, Ta Jung ^a  

^a NATIONAL CHUNG HSING UNIVERSITY   (Taiwan)

^b LANZHOU UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; HYDROLYSIS;

LACTONES;

AMINO ACIDS;

ALPHA AMINO ACID; CAMPHOR; LACTONE;

ALKYLATION; ARTICLE; CHIRALITY; ENANTIOMER; HYDROLYSIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0346665612     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026285a     Document Type: Article

References (25)

1. Xu, P.-F.; Chen, Y.-S.; Lin, T.-J. J. Org. Chem. 2002 67,2309.
2. For reviews on the asymmetric synthesis of α-amino acids, see: (a) Cativiela, C.; Diaz-de-Villegas, M. D. Tetrahedron: Asymmetry 2000, 11, 645. (b) Williams, R. M. Methods Mol. Med. 1999, 23, 339. (c) Palomo, C.; Aizpurua, J. M.; Ganboa, I.; Oiarbide, M. Amino Acids 1999, 16, 321. (d) Calmes, M.; Daunis, J. Amino acids 1999, 16, 215. (e) Seebach, D.; Hoffmann, M. Eur. J. Org. Chem. 1998, 1337, 7. (f) Wirth, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 225. (g) Meffre, P.; Le Goffic, F. Amino Acids 1996, 11, 313. (h) North, M. Contemp. Org. Synth. 1996, 3, 323. (i) Duthaler, R. O. Tetrahedron 1994, 50, 1539. (j) Cintas, P. Tetrahedron 1991, 47, 6079. (k) Lu, T.-J. Chemistry (The Chinese Chem. Soc., Taiwan China) 1992, 50, 51. (l) Williams, R. M. Synthesis of Optically Active Amino Acids; Pergamon Press: Oxford, 1989. (m) El Achqar, A.; Boumzebra, M.; Roumestant, M.-L.; Viallefont, P. Tetrahedron 1988, 44, 5319 and references cited therein.
3. For reviews on the asymmetric synthesis of α-amino acids, see: (a) Cativiela, C.; Diaz-de-Villegas, M. D. Tetrahedron: Asymmetry 2000, 11, 645. (b) Williams, R. M. Methods Mol. Med. 1999, 23, 339. (c) Palomo, C.; Aizpurua, J. M.; Ganboa, I.; Oiarbide, M. Amino Acids 1999, 16, 321. (d) Calmes, M.; Daunis, J. Amino acids 1999, 16, 215. (e) Seebach, D.; Hoffmann, M. Eur. J. Org. Chem. 1998, 1337, 7. (f) Wirth, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 225. (g) Meffre, P.; Le Goffic, F. Amino Acids 1996, 11, 313. (h) North, M. Contemp. Org. Synth. 1996, 3, 323. (i) Duthaler, R. O. Tetrahedron 1994, 50, 1539. (j) Cintas, P. Tetrahedron 1991, 47, 6079. (k) Lu, T.-J. Chemistry (The Chinese Chem. Soc., Taiwan China) 1992, 50, 51. (l) Williams, R. M. Synthesis of Optically Active Amino Acids; Pergamon Press: Oxford, 1989. (m) El Achqar, A.; Boumzebra, M.; Roumestant, M.-L.; Viallefont, P. Tetrahedron 1988, 44, 5319 and references cited therein.
4. For reviews on the asymmetric synthesis of α-amino acids, see: (a) Cativiela, C.; Diaz-de-Villegas, M. D. Tetrahedron: Asymmetry 2000, 11, 645. (b) Williams, R. M. Methods Mol. Med. 1999, 23, 339. (c) Palomo, C.; Aizpurua, J. M.; Ganboa, I.; Oiarbide, M. Amino Acids 1999, 16, 321. (d) Calmes, M.; Daunis, J. Amino acids 1999, 16, 215. (e) Seebach, D.; Hoffmann, M. Eur. J. Org. Chem. 1998, 1337, 7. (f) Wirth, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 225. (g) Meffre, P.; Le Goffic, F. Amino Acids 1996, 11, 313. (h) North, M. Contemp. Org. Synth. 1996, 3, 323. (i) Duthaler, R. O. Tetrahedron 1994, 50, 1539. (j) Cintas, P. Tetrahedron 1991, 47, 6079. (k) Lu, T.-J. Chemistry (The Chinese Chem. Soc., Taiwan China) 1992, 50, 51. (l) Williams, R. M. Synthesis of Optically Active Amino Acids; Pergamon Press: Oxford, 1989. (m) El Achqar, A.; Boumzebra, M.; Roumestant, M.-L.; Viallefont, P. Tetrahedron 1988, 44, 5319 and references cited therein.
5. For reviews on the asymmetric synthesis of α-amino acids, see: (a) Cativiela, C.; Diaz-de-Villegas, M. D. Tetrahedron: Asymmetry 2000, 11, 645. (b) Williams, R. M. Methods Mol. Med. 1999, 23, 339. (c) Palomo, C.; Aizpurua, J. M.; Ganboa, I.; Oiarbide, M. Amino Acids 1999, 16, 321. (d) Calmes, M.; Daunis, J. Amino acids 1999, 16, 215. (e) Seebach, D.; Hoffmann, M. Eur. J. Org. Chem. 1998, 1337, 7. (f) Wirth, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 225. (g) Meffre, P.; Le Goffic, F. Amino Acids 1996, 11, 313. (h) North, M. Contemp. Org. Synth. 1996, 3, 323. (i) Duthaler, R. O. Tetrahedron 1994, 50, 1539. (j) Cintas, P. Tetrahedron 1991, 47, 6079. (k) Lu, T.-J. Chemistry (The Chinese Chem. Soc., Taiwan China) 1992, 50, 51. (l) Williams, R. M. Synthesis of Optically Active Amino Acids; Pergamon Press: Oxford, 1989. (m) El Achqar, A.; Boumzebra, M.; Roumestant, M.-L.; Viallefont, P. Tetrahedron 1988, 44, 5319 and references cited therein.
6. For reviews on the asymmetric synthesis of α-amino acids, see: (a) Cativiela, C.; Diaz-de-Villegas, M. D. Tetrahedron: Asymmetry 2000, 11, 645. (b) Williams, R. M. Methods Mol. Med. 1999, 23, 339. (c) Palomo, C.; Aizpurua, J. M.; Ganboa, I.; Oiarbide, M. Amino Acids 1999, 16, 321. (d) Calmes, M.; Daunis, J. Amino acids 1999, 16, 215. (e) Seebach, D.; Hoffmann, M. Eur. J. Org. Chem. 1998, 1337, 7. (f) Wirth, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 225. (g) Meffre, P.; Le Goffic, F. Amino Acids 1996, 11, 313. (h) North, M. Contemp. Org. Synth. 1996, 3, 323. (i) Duthaler, R. O. Tetrahedron 1994, 50, 1539. (j) Cintas, P. Tetrahedron 1991, 47, 6079. (k) Lu, T.-J. Chemistry (The Chinese Chem. Soc., Taiwan China) 1992, 50, 51. (l) Williams, R. M. Synthesis of Optically Active Amino Acids; Pergamon Press: Oxford, 1989. (m) El Achqar, A.; Boumzebra, M.; Roumestant, M.-L.; Viallefont, P. Tetrahedron 1988, 44, 5319 and references cited therein.
7. For reviews on the asymmetric synthesis of α-amino acids, see: (a) Cativiela, C.; Diaz-de-Villegas, M. D. Tetrahedron: Asymmetry 2000, 11, 645. (b) Williams, R. M. Methods Mol. Med. 1999, 23, 339. (c) Palomo, C.; Aizpurua, J. M.; Ganboa, I.; Oiarbide, M. Amino Acids 1999, 16, 321. (d) Calmes, M.; Daunis, J. Amino acids 1999, 16, 215. (e) Seebach, D.; Hoffmann, M. Eur. J. Org. Chem. 1998, 1337, 7. (f) Wirth, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 225. (g) Meffre, P.; Le Goffic, F. Amino Acids 1996, 11, 313. (h) North, M. Contemp. Org. Synth. 1996, 3, 323. (i) Duthaler, R. O. Tetrahedron 1994, 50, 1539. (j) Cintas, P. Tetrahedron 1991, 47, 6079. (k) Lu, T.-J. Chemistry (The Chinese Chem. Soc., Taiwan China) 1992, 50, 51. (l) Williams, R. M. Synthesis of Optically Active Amino Acids; Pergamon Press: Oxford, 1989. (m) El Achqar, A.; Boumzebra, M.; Roumestant, M.-L.; Viallefont, P. Tetrahedron 1988, 44, 5319 and references cited therein.
8. For reviews on the asymmetric synthesis of α-amino acids, see: (a) Cativiela, C.; Diaz-de-Villegas, M. D. Tetrahedron: Asymmetry 2000, 11, 645. (b) Williams, R. M. Methods Mol. Med. 1999, 23, 339. (c) Palomo, C.; Aizpurua, J. M.; Ganboa, I.; Oiarbide, M. Amino Acids 1999, 16, 321. (d) Calmes, M.; Daunis, J. Amino acids 1999, 16, 215. (e) Seebach, D.; Hoffmann, M. Eur. J. Org. Chem. 1998, 1337, 7. (f) Wirth, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 225. (g) Meffre, P.; Le Goffic, F. Amino Acids 1996, 11, 313. (h) North, M. Contemp. Org. Synth. 1996, 3, 323. (i) Duthaler, R. O. Tetrahedron 1994, 50, 1539. (j) Cintas, P. Tetrahedron 1991, 47, 6079. (k) Lu, T.-J. Chemistry (The Chinese Chem. Soc., Taiwan China) 1992, 50, 51. (l) Williams, R. M. Synthesis of Optically Active Amino Acids; Pergamon Press: Oxford, 1989. (m) El Achqar, A.; Boumzebra, M.; Roumestant, M.-L.; Viallefont, P. Tetrahedron 1988, 44, 5319 and references cited therein.
9. For reviews on the asymmetric synthesis of α-amino acids, see: (a) Cativiela, C.; Diaz-de-Villegas, M. D. Tetrahedron: Asymmetry 2000, 11, 645. (b) Williams, R. M. Methods Mol. Med. 1999, 23, 339. (c) Palomo, C.; Aizpurua, J. M.; Ganboa, I.; Oiarbide, M. Amino Acids 1999, 16, 321. (d) Calmes, M.; Daunis, J. Amino acids 1999, 16, 215. (e) Seebach, D.; Hoffmann, M. Eur. J. Org. Chem. 1998, 1337, 7. (f) Wirth, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 225. (g) Meffre, P.; Le Goffic, F. Amino Acids 1996, 11, 313. (h) North, M. Contemp. Org. Synth. 1996, 3, 323. (i) Duthaler, R. O. Tetrahedron 1994, 50, 1539. (j) Cintas, P. Tetrahedron 1991, 47, 6079. (k) Lu, T.-J. Chemistry (The Chinese Chem. Soc., Taiwan China) 1992, 50, 51. (l) Williams, R. M. Synthesis of Optically Active Amino Acids; Pergamon Press: Oxford, 1989. (m) El Achqar, A.; Boumzebra, M.; Roumestant, M.-L.; Viallefont, P. Tetrahedron 1988, 44, 5319 and references cited therein.
10. For reviews on the asymmetric synthesis of α-amino acids, see: (a) Cativiela, C.; Diaz-de-Villegas, M. D. Tetrahedron: Asymmetry 2000, 11, 645. (b) Williams, R. M. Methods Mol. Med. 1999, 23, 339. (c) Palomo, C.; Aizpurua, J. M.; Ganboa, I.; Oiarbide, M. Amino Acids 1999, 16, 321. (d) Calmes, M.; Daunis, J. Amino acids 1999, 16, 215. (e) Seebach, D.; Hoffmann, M. Eur. J. Org. Chem. 1998, 1337, 7. (f) Wirth, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 225. (g) Meffre, P.; Le Goffic, F. Amino Acids 1996, 11, 313. (h) North, M. Contemp. Org. Synth. 1996, 3, 323. (i) Duthaler, R. O. Tetrahedron 1994, 50, 1539. (j) Cintas, P. Tetrahedron 1991, 47, 6079. (k) Lu, T.-J. Chemistry (The Chinese Chem. Soc., Taiwan China) 1992, 50, 51. (l) Williams, R. M. Synthesis of Optically Active Amino Acids; Pergamon Press: Oxford, 1989. (m) El Achqar, A.; Boumzebra, M.; Roumestant, M.-L.; Viallefont, P. Tetrahedron 1988, 44, 5319 and references cited therein.
11. For reviews on the asymmetric synthesis of α-amino acids, see: (a) Cativiela, C.; Diaz-de-Villegas, M. D. Tetrahedron: Asymmetry 2000, 11, 645. (b) Williams, R. M. Methods Mol. Med. 1999, 23, 339. (c) Palomo, C.; Aizpurua, J. M.; Ganboa, I.; Oiarbide, M. Amino Acids 1999, 16, 321. (d) Calmes, M.; Daunis, J. Amino acids 1999, 16, 215. (e) Seebach, D.; Hoffmann, M. Eur. J. Org. Chem. 1998, 1337, 7. (f) Wirth, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 225. (g) Meffre, P.; Le Goffic, F. Amino Acids 1996, 11, 313. (h) North, M. Contemp. Org. Synth. 1996, 3, 323. (i) Duthaler, R. O. Tetrahedron 1994, 50, 1539. (j) Cintas, P. Tetrahedron 1991, 47, 6079. (k) Lu, T.-J. Chemistry (The Chinese Chem. Soc., Taiwan China) 1992, 50, 51. (l) Williams, R. M. Synthesis of Optically Active Amino Acids; Pergamon Press: Oxford, 1989. (m) El Achqar, A.; Boumzebra, M.; Roumestant, M.-L.; Viallefont, P. Tetrahedron 1988, 44, 5319 and references cited therein.
12. For reviews on the asymmetric synthesis of α-amino acids, see: (a) Cativiela, C.; Diaz-de-Villegas, M. D. Tetrahedron: Asymmetry 2000, 11, 645. (b) Williams, R. M. Methods Mol. Med. 1999, 23, 339. (c) Palomo, C.; Aizpurua, J. M.; Ganboa, I.; Oiarbide, M. Amino Acids 1999, 16, 321. (d) Calmes, M.; Daunis, J. Amino acids 1999, 16, 215. (e) Seebach, D.; Hoffmann, M. Eur. J. Org. Chem. 1998, 1337, 7. (f) Wirth, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 225. (g) Meffre, P.; Le Goffic, F. Amino Acids 1996, 11, 313. (h) North, M. Contemp. Org. Synth. 1996, 3, 323. (i) Duthaler, R. O. Tetrahedron 1994, 50, 1539. (j) Cintas, P. Tetrahedron 1991, 47, 6079. (k) Lu, T.-J. Chemistry (The Chinese Chem. Soc., Taiwan China) 1992, 50, 51. (l) Williams, R. M. Synthesis of Optically Active Amino Acids; Pergamon Press: Oxford, 1989. (m) El Achqar, A.; Boumzebra, M.; Roumestant, M.-L.; Viallefont, P. Tetrahedron 1988, 44, 5319 and references cited therein.
13. For reviews on the asymmetric synthesis of α-amino acids, see: (a) Cativiela, C.; Diaz-de-Villegas, M. D. Tetrahedron: Asymmetry 2000, 11, 645. (b) Williams, R. M. Methods Mol. Med. 1999, 23, 339. (c) Palomo, C.; Aizpurua, J. M.; Ganboa, I.; Oiarbide, M. Amino Acids 1999, 16, 321. (d) Calmes, M.; Daunis, J. Amino acids 1999, 16, 215. (e) Seebach, D.; Hoffmann, M. Eur. J. Org. Chem. 1998, 1337, 7. (f) Wirth, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 225. (g) Meffre, P.; Le Goffic, F. Amino Acids 1996, 11, 313. (h) North, M. Contemp. Org. Synth. 1996, 3, 323. (i) Duthaler, R. O. Tetrahedron 1994, 50, 1539. (j) Cintas, P. Tetrahedron 1991, 47, 6079. (k) Lu, T.-J. Chemistry (The Chinese Chem. Soc., Taiwan China) 1992, 50, 51. (l) Williams, R. M. Synthesis of Optically Active Amino Acids; Pergamon Press: Oxford, 1989. (m) El Achqar, A.; Boumzebra, M.; Roumestant, M.-L.; Viallefont, P. Tetrahedron 1988, 44, 5319 and references cited therein.
14. For reviews on the asymmetric synthesis of α-amino acids, see: (a) Cativiela, C.; Diaz-de-Villegas, M. D. Tetrahedron: Asymmetry 2000, 11, 645. (b) Williams, R. M. Methods Mol. Med. 1999, 23, 339. (c) Palomo, C.; Aizpurua, J. M.; Ganboa, I.; Oiarbide, M. Amino Acids 1999, 16, 321. (d) Calmes, M.; Daunis, J. Amino acids 1999, 16, 215. (e) Seebach, D.; Hoffmann, M. Eur. J. Org. Chem. 1998, 1337, 7. (f) Wirth, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 225. (g) Meffre, P.; Le Goffic, F. Amino Acids 1996, 11, 313. (h) North, M. Contemp. Org. Synth. 1996, 3, 323. (i) Duthaler, R. O. Tetrahedron 1994, 50, 1539. (j) Cintas, P. Tetrahedron 1991, 47, 6079. (k) Lu, T.-J. Chemistry (The Chinese Chem. Soc., Taiwan China) 1992, 50, 51. (l) Williams, R. M. Synthesis of Optically Active Amino Acids; Pergamon Press: Oxford, 1989. (m) El Achqar, A.; Boumzebra, M.; Roumestant, M.-L.; Viallefont, P. Tetrahedron 1988, 44, 5319 and references cited therein.
15. Tanaka, K.; Uno, H.; Osuga, H.; Suzuki, H. Tetrahedron: Asymmetry 1993, 4, 629.
16. (a) Kouklovsky, C.; Pouilhes, A.; Langlois, Y. J. Am. Chem. Soc. 1990, 112, 6672. (b) Banks, M. R.; Blake, A. J.; Cadogan, J. I. G.; Doyle, A. A.; Gosney, I.; Hodgson, P. K. G.; Thorburn, P. Tetrahedron 1996, 52, 4079. Reduction utilizing the procedures reported in these two articles afforded the desired 3-exo-hydroxycamphor and the 2-exohydroxyepicamphor in a 6:1 ratio in a combined yield of 90%. Morris and Ryder also have pointed out that they and Professor G. Helmchen's laboratories were unable to reproduce Professor Langlois's results (Morris, D. G.; Ryder, K. S. Synthesis 1997, 620).
17. (a) Kouklovsky, C.; Pouilhes, A.; Langlois, Y. J. Am. Chem. Soc. 1990, 112, 6672. (b) Banks, M. R.; Blake, A. J.; Cadogan, J. I. G.; Doyle, A. A.; Gosney, I.; Hodgson, P. K. G.; Thorburn, P. Tetrahedron 1996, 52, 4079. Reduction utilizing the procedures reported in these two articles afforded the desired 3-exo-hydroxycamphor and the 2-exohydroxyepicamphor in a 6:1 ratio in a combined yield of 90%. Morris and Ryder also have pointed out that they and Professor G. Helmchen's laboratories were unable to reproduce Professor Langlois's results (Morris, D. G.; Ryder, K. S. Synthesis 1997, 620).
18. (a) Kouklovsky, C.; Pouilhes, A.; Langlois, Y. J. Am. Chem. Soc. 1990, 112, 6672. (b) Banks, M. R.; Blake, A. J.; Cadogan, J. I. G.; Doyle, A. A.; Gosney, I.; Hodgson, P. K. G.; Thorburn, P. Tetrahedron 1996, 52, 4079. Reduction utilizing the procedures reported in these two articles afforded the desired 3-exo-hydroxycamphor and the 2-exohydroxyepicamphor in a 6:1 ratio in a combined yield of 90%. Morris and Ryder also have pointed out that they and Professor G. Helmchen's laboratories were unable to reproduce Professor Langlois's results (Morris, D. G.; Ryder, K. S. Synthesis 1997, 620).
19. When camphorquinone was refluxed in toluene under similar conditions for 10 h gave the diacetal (39%) and a mixture of two monoacetals (60%).
20. Verdaguer, X.; Marchueta, I.; Tormo, J.; Moyano, A.; Pericàs, M. A.; Riera, A. Helv. Chim. Acta 1998, 81, 78.
21. The optimum conditions for the alkylation of iminolactone reported in ref 1 were used in this study.
22. This served as a strong indication that the alkylation of the enolate occurred exclusively from the bottom face. The NMR spectrum of the crude methylation reaction was examined very carefully and there was no sign of the exo-methylated product as far as the NMR detection limit can tell.
23. Similar trend also was observed in the alkylation of iminolactone 1, see ref 1.
24. Michael N. Burnett and Carroll K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid Plot Program for Crystal Structure Illustrations, Oak Ridge National Laboratory Report ORNL-6895, 1996.
25. Chinchilla, R.; Falvello, L. R.; Galindo, N.; Nájera, C. Tetrahedron: Asymmetry 1998, 9, 2223.