1,3-Dipolar cycloadditions to unsymmetrical ketone-derived chiral stabilized azomethine ylides: Strategies for the synthesis of highly substituted amino acids

Synthesis

Volumn , Issue 19, 2005, Pages 3271-3278

  Aldous, David J ^a   Drew, Michael G B ^b   Draffin, William N ^b   Hamelin, Estelle M N ^b   Harwood, Laurence M ^b   Thurairatnam, Sukanthini ^a  

^a Rhone Poulenc Rorer Ctrl Research   (United Kingdom)

^b UNIVERSITY OF READING   (United Kingdom)

Author keywords

hydroxy amino acid; Azomethine ylide; Cycloaddition; Intramolecular; Proline

Indexed keywords

AMINO ACIDS; KETONES; SYNTHESIS (CHEMICAL);

Β-HYDROXY-Α-AMINO ACID; AZOMETHINE YLIDE; PROLINE;

ORGANIC COMPOUNDS;

AMINO ACID DERIVATIVE; AZOMETHINE YLIDE; BETA HYDROXY ALPHA AMINO ACID; KETONE; PROLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; CYCLOADDITION; ENANTIOMER; SYNTHESIS;

EID: 29044444299     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-918487     Document Type: Article

References (26)

1. Aldous, D. J. ; Drew, M. G. B. ; Hamelin, E. M.-N. ; Harwood, L. M.; Jahans, A. B.; Thurairatnam, S. Synlett 2001, 1836.
2. For examples of the synthesis of substituted prolines, see: (a) Koskinen, A. M. P.; Helaja, J.; Kumpulainen, T. T.; Koivisto, J.; Mansikkamaki, H.; Rissanen, K. J. Org Chem. 2005, in press.
3. (b) Seebach, D.; Boes, M.; Naef, R.; Schwiezer, W. B. J. Am. Chem. Soc. 1983, 105, 5390.
4. (c) Wang, Q.; Tran Huu Dau, M.-E.; Saski, A.; Potier, P. Tetrahedron 2001, 30, 6455.
5. (d) Flamant-Rabin, C.; Wang, Q.; Chiaroni, A.; Sasaki, A. Tetrahedron 2002, 58, 10475.
6. (e) Maeda, K.; Miller, R. A.; Szumigala, R. H. Jr.; Shafiee, A.; Karady, S.; Armstrong, J. D. III Tetrahedron Lett. 2005, 46, 1545.
7. (f) Xia, Q.; Ganem, B. Tetrahedron Lett. 2002, 43, 1597.
8. (g) An, S. S. A.; Lester, C. C.; Peng, J.-L.; Li, Y.-J.; Rothwarf, D. M.; Welker, E.; Thannhauser, T. W.; Zhang, L. S.; Tam, J. P.; Scheraga, H. A. J. Am. Chem. Soc. 1999, 121, 11558.
9. (h) Magaard, V. W.; Sanchez, R. M.; Bean, J. W.; Moore, M. L. Tetrahedron Lett. 1993, 34, 381.
10. Bonnett, R.; Clark, V. M.; Giddey, A.; Todd, S. A. J. Chem. Soc. 1959, 2087.
11. (j) Xia, Q.; Ganem, B. Tetrahedron Lett. 2002, 43, 1597.
12. (k) Elardi, J.; Jackson, W. R.; Robinson, A. J. Tetrahedron: Asymmetry 2005, 16, 2025.
13. Che, Y.; Marshall, R. J. Org. Chem. 2004, 69, 9030.
14. Gil, A. M.; Bunuel, E.; Jimenez, A. I.; Cativiela, C. Tetrahedron Lett. 2003, 32, 5999.
15. Coldham, I.; Hufton, R. Chem. Rev. 2005, 105, 2765.
16. (a) Harwood, L. M.; Lilley, I. A. Tetrahedron Lett. 1993, 34, 537.
17. (b) Harwood, L. M.; Kitchen, L. C. Tetrahedron Lett. 1993, 34, 6603.
18. (c) Harwood, L. M.; Lilley, I. A. Synlett 1996, 1010.
19. 3, 6487 independent reflections were collected. The structure was solved by direct methods and refined on F2 to R1 0.0996, wR2 0.2057. Atomic co-ordinates, bond lengths and angles and thermal parameters have been deposited with the Cambridge Crystallographic Service.
20. Kabsch, W. J. Appl. Cryst. 1988, 21, 916.
21. Sheldrick, G. M. Acta Cryst 1990, A46, 467.
22. Sheldrick, G. M. Program for Crystal Structure Refinement; University of Göttingen: Göttingen, 1993.
23. Harwood, L. M.; Manage, A. C.; Robin, S.; Hopes, S. F. G.; Watkin, D. J.; Williams, C. E. Synlett 1993, 777.
24. Anslow, A. S.; Harwood, L. M.; Phillips, H.; Watkin, D. J.; Wong, L. F. Tetrahedron: Asymmetry 1991, 2, 1343.
25. (a) Harwood, L. M.; Macro, J.; Watkin, D.; Williams, C. E.; Wong, L. F. Tetrahedron: Asymmetry 1992, 3, 1127.
26. (b) Alker, D.; Hamblett, G.; Harwood, L. M.; Robertson, S. M.; Watkin, D. J.; Williams, C. E. Tetrahedron 1998, 54, 6089.