PTC and organic bases-LiCl assisted alkylation of imidazolidinone- glycine iminic derivatives for the asymmetric synthesis of α-amino acids

Tetrahedron Asymmetry

Volumn 9, Issue 22, 1998, Pages 3935-3938

  Guillena, Gabriela ^a   Nájera, Carmen ^a  

^a UNIVERSITY OF ALICANTE   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; ALPHA AMINO ACID; BASE; GLYCINE DERIVATIVE; HALIDE; IMIDAZOLIDINE DERIVATIVE; LITHIUM CHLORIDE;

ALKYLATION; AMINO ACID SYNTHESIS; ARTICLE; DIASTEREOISOMER; HYDROLYSIS; PHASE TRANSITION; PRIORITY JOURNAL;

EID: 0344474528     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00402-9     Document Type: Article

References (42)

1. Recent review s: (a) Williams, R. M. Synthesis of Optically Active Amino Acids, Pergamon: Oxford, 1989. (b) Heimgartner, H. Angew. Chem., Int. Ed. Engl. 1991, 30, 238-264. (c) Duthaler, R. O. Tetrahedron 1994, 50, 1540-1650. (d) Noth, M. Contemp. Org. Synth. 1996, 323. (e) Seebach, D.; Sting, A. R.; Hoffmann, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2708-2748. (f) Wirth, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 225-227.
2. Recent review s: (a) Williams, R. M. Synthesis of Optically Active Amino Acids, Pergamon: Oxford, 1989. (b) Heimgartner, H. Angew. Chem., Int. Ed. Engl. 1991, 30, 238-264. (c) Duthaler, R. O. Tetrahedron 1994, 50, 1540-1650. (d) Noth, M. Contemp. Org. Synth. 1996, 323. (e) Seebach, D.; Sting, A. R.; Hoffmann, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2708-2748. (f) Wirth, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 225-227.
3. Recent review s: (a) Williams, R. M. Synthesis of Optically Active Amino Acids, Pergamon: Oxford, 1989. (b) Heimgartner, H. Angew. Chem., Int. Ed. Engl. 1991, 30, 238-264. (c) Duthaler, R. O. Tetrahedron 1994, 50, 1540-1650. (d) Noth, M. Contemp. Org. Synth. 1996, 323. (e) Seebach, D.; Sting, A. R.; Hoffmann, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2708-2748. (f) Wirth, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 225-227.
4. Recent review s: (a) Williams, R. M. Synthesis of Optically Active Amino Acids, Pergamon: Oxford, 1989. (b) Heimgartner, H. Angew. Chem., Int. Ed. Engl. 1991, 30, 238-264. (c) Duthaler, R. O. Tetrahedron 1994, 50, 1540-1650. (d) Noth, M. Contemp. Org. Synth. 1996, 323. (e) Seebach, D.; Sting, A. R.; Hoffmann, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2708-2748. (f) Wirth, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 225-227.
5. Recent review s: (a) Williams, R. M. Synthesis of Optically Active Amino Acids, Pergamon: Oxford, 1989. (b) Heimgartner, H. Angew. Chem., Int. Ed. Engl. 1991, 30, 238-264. (c) Duthaler, R. O. Tetrahedron 1994, 50, 1540-1650. (d) Noth, M. Contemp. Org. Synth. 1996, 323. (e) Seebach, D.; Sting, A. R.; Hoffmann, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2708-2748. (f) Wirth, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 225-227.
6. Recent review s: (a) Williams, R. M. Synthesis of Optically Active Amino Acids, Pergamon: Oxford, 1989. (b) Heimgartner, H. Angew. Chem., Int. Ed. Engl. 1991, 30, 238-264. (c) Duthaler, R. O. Tetrahedron 1994, 50, 1540-1650. (d) Noth, M. Contemp. Org. Synth. 1996, 323. (e) Seebach, D.; Sting, A. R.; Hoffmann, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2708-2748. (f) Wirth, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 225-227.
7. Phase-Transfer Catalysis, Halpern, M. E., Ed., ACS: Washington, 1997.
8. (a) Oppolzer, W.; Moretti, R.; Thomi, S. Tetrahedron Lett. 1989, 29, 6009-6010.
9. (b) Oppolzer, W.; Moretti, R.; Zhon, C. Helv. Chim. Acta 1994, 77, 2363-2380.
10. (c) Ayoub, M.; Chassaing, G.; Loffet, A.; Lavielle, S. Tetrahedron Lett. 1995, 36, 4069-4072.
11. Chinchilla, R.; Falvello, L. R.; Galindo, N.; Nájera, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 995-997.
12. Abellán, T.; Nájera, C.; Sansano, J. M. Tetrahedron: Asymmetry 1998, 9, 2211-2214.
13. (a) O'Donnell, M. J.; Bennett, W. D.; Wu, S. J. Am. Chem. Soc. 1989, 111, 2353-2355.
14. (b) Gasparsky, C. M.; Miller, M. J. Tetrahedron Lett. 1991, 47, 5367-5378.
15. (c) Lipkowitz, K. B.; Cavanaugh, M. W.; Baker, B.; O'Donnell, M. J. J. Org. Chem. 1991, 56, 5181-5192.
16. (d) O'Donnell, M. J.; Wu, S. Tetrahedron: Asymmetry 1992, 3, 591-594.
17. (e) Imperiali, B.; Fisher, S. L. J. Org. Chem. 1992, 57, 757-759.
18. (f) Imperiali, B.; Prins, T. J.; Fisher, S. L. J. Org. Chem. 1993, 58, 1613-1616.
19. (g) O'Donnell, M. J.; Wu, S.; Huffmann, J. C. Tetrahedron 1994, 50, 4507-4518.
20. (h) Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414-12415.
21. (i) Lygo, B.; Wainwright, P. G. Tetrahedron Lett. 1997, 38, 8595-8598.
22. Belokon', Y. N.; Kochetkov, K. A.; Churkina, T. D.; Ikonnikov, N. S.; Chesnokov, A. A.; Larionov, O. V.; Parmar, V. S.; Kumar, R.; Kagan, H. B. Tetrahedron: Asymmetry 1998, 9, 851-857.
23. Schwesinger, R.; Willaredt, J.; Schlemper, H.; Keller, M.; Schmitt, D.; Fritz, H. Chem. Ber. 1994, 127, 2435-2454, and references cited therein.
24. This base has been used in the alkylation of the resin-bound benzophenone glycine imine: (a) O'Donnell, M. J.; Lugar, C. W.; Pottorf, R. S.; Zhou, C.; Scott, W. L.; Cwi, C. L. Tetrahedron Lett. 1997, 38, 7163-7166. (b) Dominguez, E.; O'Donnell, M. J.; Scott, W. L. Tetrahedron Lett. 1998, 39, 2167-2170.
25. This base has been used in the alkylation of the resin-bound benzophenone glycine imine: (a) O'Donnell, M. J.; Lugar, C. W.; Pottorf, R. S.; Zhou, C.; Scott, W. L.; Cwi, C. L. Tetrahedron Lett. 1997, 38, 7163-7166. (b) Dominguez, E.; O'Donnell, M. J.; Scott, W. L. Tetrahedron Lett. 1998, 39, 2167-2170.
26. Chinchilla, R.; Galindo, N.; Nájera, C. Tetrahedron: Asymmetry 1998, 9, 2769-2772.
27. Easily prepared from (-)-ephedrinium chloride and urea: Roder, H.; Helmchen, G.; Peters, E. M.; von Schnering, H. G. Angew. Chem., Int. Ed. Engl. 1984, 23, 898-899.
28. For applications of this chiral auxiliary in asymmetric synthesis see for instance: (a) Cardillo, G.; D'Amico, A.; Orena, M.; Sandri, S. J. Org. Chem. 1988, 53, 2354-2356. (b) Melnyk, O.; Stephan, E.; Pourcelot, G.; Cresson, P. Tetrahedron 1992, 48, 841-850. (c) Jensen, K. N.; Roos, G. H. P. Tetrahedron: Asymmetry 1992, 3, 1553-1554. (d) Drewes, S. E.; Malissar, D. G. S.; Roos, G. H. P. Chem. Ber. 1993, 126, 2663-2673. (e) Cardillo, G.; De Simone, A.; Gentilucci, L.; Sabatino, P.; Tomasini, C. Tetrahedron Lett. 1994, 35, 5051-5054. (f) van Heerden, P. S.; Bezuidenhoudt, B. C. B.; Ferreira, D. Tetrahedron Lett. 1997, 38, 1821-1824. (g) Bongini, A.; Cardillo, G.; Gentilucci, L.; Tomasini, C. J. Org. Chem. 1997, 62, 9148-9153. (h) Trost, B. M.; Ceschi, M. A.; König, B. Angew. Chem., Int. Ed. Engl. 1997, 36, 1486-1489.
29. For applications of this chiral auxiliary in asymmetric synthesis see for instance: (a) Cardillo, G.; D'Amico, A.; Orena, M.; Sandri, S. J. Org. Chem. 1988, 53, 2354-2356. (b) Melnyk, O.; Stephan, E.; Pourcelot, G.; Cresson, P. Tetrahedron 1992, 48, 841-850. (c) Jensen, K. N.; Roos, G. H. P. Tetrahedron: Asymmetry 1992, 3, 1553-1554. (d) Drewes, S. E.; Malissar, D. G. S.; Roos, G. H. P. Chem. Ber. 1993, 126, 2663-2673. (e) Cardillo, G.; De Simone, A.; Gentilucci, L.; Sabatino, P.; Tomasini, C. Tetrahedron Lett. 1994, 35, 5051-5054. (f) van Heerden, P. S.; Bezuidenhoudt, B. C. B.; Ferreira, D. Tetrahedron Lett. 1997, 38, 1821-1824. (g) Bongini, A.; Cardillo, G.; Gentilucci, L.; Tomasini, C. J. Org. Chem. 1997, 62, 9148-9153. (h) Trost, B. M.; Ceschi, M. A.; König, B. Angew. Chem., Int. Ed. Engl. 1997, 36, 1486-1489.
30. For applications of this chiral auxiliary in asymmetric synthesis see for instance: (a) Cardillo, G.; D'Amico, A.; Orena, M.; Sandri, S. J. Org. Chem. 1988, 53, 2354-2356. (b) Melnyk, O.; Stephan, E.; Pourcelot, G.; Cresson, P. Tetrahedron 1992, 48, 841-850. (c) Jensen, K. N.; Roos, G. H. P. Tetrahedron: Asymmetry 1992, 3, 1553-1554. (d) Drewes, S. E.; Malissar, D. G. S.; Roos, G. H. P. Chem. Ber. 1993, 126, 2663-2673. (e) Cardillo, G.; De Simone, A.; Gentilucci, L.; Sabatino, P.; Tomasini, C. Tetrahedron Lett. 1994, 35, 5051-5054. (f) van Heerden, P. S.; Bezuidenhoudt, B. C. B.; Ferreira, D. Tetrahedron Lett. 1997, 38, 1821-1824. (g) Bongini, A.; Cardillo, G.; Gentilucci, L.; Tomasini, C. J. Org. Chem. 1997, 62, 9148-9153. (h) Trost, B. M.; Ceschi, M. A.; König, B. Angew. Chem., Int. Ed. Engl. 1997, 36, 1486-1489.
31. For applications of this chiral auxiliary in asymmetric synthesis see for instance: (a) Cardillo, G.; D'Amico, A.; Orena, M.; Sandri, S. J. Org. Chem. 1988, 53, 2354-2356. (b) Melnyk, O.; Stephan, E.; Pourcelot, G.; Cresson, P. Tetrahedron 1992, 48, 841-850. (c) Jensen, K. N.; Roos, G. H. P. Tetrahedron: Asymmetry 1992, 3, 1553-1554. (d) Drewes, S. E.; Malissar, D. G. S.; Roos, G. H. P. Chem. Ber. 1993, 126, 2663-2673. (e) Cardillo, G.; De Simone, A.; Gentilucci, L.; Sabatino, P.; Tomasini, C. Tetrahedron Lett. 1994, 35, 5051-5054. (f) van Heerden, P. S.; Bezuidenhoudt, B. C. B.; Ferreira, D. Tetrahedron Lett. 1997, 38, 1821-1824. (g) Bongini, A.; Cardillo, G.; Gentilucci, L.; Tomasini, C. J. Org. Chem. 1997, 62, 9148-9153. (h) Trost, B. M.; Ceschi, M. A.; König, B. Angew. Chem., Int. Ed. Engl. 1997, 36, 1486-1489.
32. For applications of this chiral auxiliary in asymmetric synthesis see for instance: (a) Cardillo, G.; D'Amico, A.; Orena, M.; Sandri, S. J. Org. Chem. 1988, 53, 2354-2356. (b) Melnyk, O.; Stephan, E.; Pourcelot, G.; Cresson, P. Tetrahedron 1992, 48, 841-850. (c) Jensen, K. N.; Roos, G. H. P. Tetrahedron: Asymmetry 1992, 3, 1553-1554. (d) Drewes, S. E.; Malissar, D. G. S.; Roos, G. H. P. Chem. Ber. 1993, 126, 2663-2673. (e) Cardillo, G.; De Simone, A.; Gentilucci, L.; Sabatino, P.; Tomasini, C. Tetrahedron Lett. 1994, 35, 5051-5054. (f) van Heerden, P. S.; Bezuidenhoudt, B. C. B.; Ferreira, D. Tetrahedron Lett. 1997, 38, 1821-1824. (g) Bongini, A.; Cardillo, G.; Gentilucci, L.; Tomasini, C. J. Org. Chem. 1997, 62, 9148-9153. (h) Trost, B. M.; Ceschi, M. A.; König, B. Angew. Chem., Int. Ed. Engl. 1997, 36, 1486-1489.
33. For applications of this chiral auxiliary in asymmetric synthesis see for instance: (a) Cardillo, G.; D'Amico, A.; Orena, M.; Sandri, S. J. Org. Chem. 1988, 53, 2354-2356. (b) Melnyk, O.; Stephan, E.; Pourcelot, G.; Cresson, P. Tetrahedron 1992, 48, 841-850. (c) Jensen, K. N.; Roos, G. H. P. Tetrahedron: Asymmetry 1992, 3, 1553-1554. (d) Drewes, S. E.; Malissar, D. G. S.; Roos, G. H. P. Chem. Ber. 1993, 126, 2663-2673. (e) Cardillo, G.; De Simone, A.; Gentilucci, L.; Sabatino, P.; Tomasini, C. Tetrahedron Lett. 1994, 35, 5051-5054. (f) van Heerden, P. S.; Bezuidenhoudt, B. C. B.; Ferreira, D. Tetrahedron Lett. 1997, 38, 1821-1824. (g) Bongini, A.; Cardillo, G.; Gentilucci, L.; Tomasini, C. J. Org. Chem. 1997, 62, 9148-9153. (h) Trost, B. M.; Ceschi, M. A.; König, B. Angew. Chem., Int. Ed. Engl. 1997, 36, 1486-1489.
34. For applications of this chiral auxiliary in asymmetric synthesis see for instance: (a) Cardillo, G.; D'Amico, A.; Orena, M.; Sandri, S. J. Org. Chem. 1988, 53, 2354-2356. (b) Melnyk, O.; Stephan, E.; Pourcelot, G.; Cresson, P. Tetrahedron 1992, 48, 841-850. (c) Jensen, K. N.; Roos, G. H. P. Tetrahedron: Asymmetry 1992, 3, 1553-1554. (d) Drewes, S. E.; Malissar, D. G. S.; Roos, G. H. P. Chem. Ber. 1993, 126, 2663-2673. (e) Cardillo, G.; De Simone, A.; Gentilucci, L.; Sabatino, P.; Tomasini, C. Tetrahedron Lett. 1994, 35, 5051-5054. (f) van Heerden, P. S.; Bezuidenhoudt, B. C. B.; Ferreira, D. Tetrahedron Lett. 1997, 38, 1821-1824. (g) Bongini, A.; Cardillo, G.; Gentilucci, L.; Tomasini, C. J. Org. Chem. 1997, 62, 9148-9153. (h) Trost, B. M.; Ceschi, M. A.; König, B. Angew. Chem., Int. Ed. Engl. 1997, 36, 1486-1489.
35. For applications of this chiral auxiliary in asymmetric synthesis see for instance: (a) Cardillo, G.; D'Amico, A.; Orena, M.; Sandri, S. J. Org. Chem. 1988, 53, 2354-2356. (b) Melnyk, O.; Stephan, E.; Pourcelot, G.; Cresson, P. Tetrahedron 1992, 48, 841-850. (c) Jensen, K. N.; Roos, G. H. P. Tetrahedron: Asymmetry 1992, 3, 1553-1554. (d) Drewes, S. E.; Malissar, D. G. S.; Roos, G. H. P. Chem. Ber. 1993, 126, 2663-2673. (e) Cardillo, G.; De Simone, A.; Gentilucci, L.; Sabatino, P.; Tomasini, C. Tetrahedron Lett. 1994, 35, 5051-5054. (f) van Heerden, P. S.; Bezuidenhoudt, B. C. B.; Ferreira, D. Tetrahedron Lett. 1997, 38, 1821-1824. (g) Bongini, A.; Cardillo, G.; Gentilucci, L.; Tomasini, C. J. Org. Chem. 1997, 62, 9148-9153. (h) Trost, B. M.; Ceschi, M. A.; König, B. Angew. Chem., Int. Ed. Engl. 1997, 36, 1486-1489.
36. Guillena, G.; Nájera, C. Tetrahedron: Asymmetry 1998, 9, 1125-1129.
37. 2 at room temperature. (equation presented)
38. 13
39. 10
40. 13
41. Ees were analysed by HPLC using a Crownpak CR (+) column.
42. Slight partial racemization was observed during the hydrolysis.