Stereoselective reactions of N-(9-phenylfluoren-9-yl)-4-oxoproline enolates. An expedient route for the preparation of conformationally restricted amino acid analogues

Journal of Organic Chemistry

Volumn 64, Issue 24, 1999, Pages 8786-8793

  Blanco, María Jesús ^a   Paleo, M Rita ^a   Penide, Celia ^a   Sardina, F Javier ^a  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

PROLINE DERIVATIVE;

ALKYLATION; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; POLYMERIZATION; STEREOCHEMISTRY;

EID: 0033607713     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990283h     Document Type: Article

References (32)

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3. (c) Sharma, R.; Lubell, W. D. J. Org. Chem. 1996, 61, 202, and references therein.
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7. (c) Samanen, J.; Zuber, G.; Bean, J.; Eggleston, D.; Romoff, T.; Kopple, K.; Saunders: M.; Regoli, D. Int. J. Pept. Protein Res. 1990, 35, 501.
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9. Beausoleil, E.; Sharma, R.; Michnick, S. W.; Lubell, W. D. J. Org. Chem. 1998, 63, 6572.
10. For a review on the use of 4-hydroxyproline in synthesis see: Remuzon, P. Tetrahedron 1996, 52, 13803.
11. (a) Blanco, M.-J.; Sardina, F. J. J. Org. Chem. 1896, 61, 4748.
12. (b) Blanco, M.-J.; Sardina, F. J. Tetrahedron Lett. 1994, 35, 8493.
13. Blanco, M.-J.; Sardina, F. J. J. Org. Chem. 1998, 63, 3411.
14. Gill, P.; Lubell, W. D. J. Org. Chem. 1995, 60, 2658.
15. A closely related approach has been used for the synthesis of kainic acid analogues: (a) Baldwin, J. E.; Fryer, A. M.; Spyvee, M. R.; Whitehead, R. C.; Wood, M. E. Tetrahedron Lett. 1996, 37, 6923. (b) Baldwin, J. E.; Bamford, S. J.; Fryer, A. M.; Wood, M. E. Tetrahedron Lett. 1995, 36, 4869. (c) Baldwin, J. E.; Rudolph, M. Tetrahedron Lett. 1994, 35, 6163. (d) Gill, P.; Lubell, W. D. J. Org. Chem. 1995, 60, 2658.
16. A closely related approach has been used for the synthesis of kainic acid analogues: (a) Baldwin, J. E.; Fryer, A. M.; Spyvee, M. R.; Whitehead, R. C.; Wood, M. E. Tetrahedron Lett. 1996, 37, 6923. (b) Baldwin, J. E.; Bamford, S. J.; Fryer, A. M.; Wood, M. E. Tetrahedron Lett. 1995, 36, 4869. (c) Baldwin, J. E.; Rudolph, M. Tetrahedron Lett. 1994, 35, 6163. (d) Gill, P.; Lubell, W. D. J. Org. Chem. 1995, 60, 2658.
17. A closely related approach has been used for the synthesis of kainic acid analogues: (a) Baldwin, J. E.; Fryer, A. M.; Spyvee, M. R.; Whitehead, R. C.; Wood, M. E. Tetrahedron Lett. 1996, 37, 6923. (b) Baldwin, J. E.; Bamford, S. J.; Fryer, A. M.; Wood, M. E. Tetrahedron Lett. 1995, 36, 4869. (c) Baldwin, J. E.; Rudolph, M. Tetrahedron Lett. 1994, 35, 6163. (d) Gill, P.; Lubell, W. D. J. Org. Chem. 1995, 60, 2658.
18. A closely related approach has been used for the synthesis of kainic acid analogues: (a) Baldwin, J. E.; Fryer, A. M.; Spyvee, M. R.; Whitehead, R. C.; Wood, M. E. Tetrahedron Lett. 1996, 37, 6923. (b) Baldwin, J. E.; Bamford, S. J.; Fryer, A. M.; Wood, M. E. Tetrahedron Lett. 1995, 36, 4869. (c) Baldwin, J. E.; Rudolph, M. Tetrahedron Lett. 1994, 35, 6163. (d) Gill, P.; Lubell, W. D. J. Org. Chem. 1995, 60, 2658.
19. 1H NMR spectra (500 MHz) of the crude reaction mixtures. Doping experiments using known amounts of various substituted proline methyl esters showed that the limit of detection was ≤2%.
20. Heathcock, C. H. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol 3, pp 111-212.
21. Mauger, A. B.; Irreverre, F.; Witkop, B. J. Am. Chem. Soc. 1966, 88, 2019.
22. For an explanation of the origin of the stereoselectivity in the reduction of the C-4 carbonyl group in 4-oxoprolines, see ref 6.
23. These results are consistent with a chelated-chair transition state. Zimmerman, H. E.; Traxler, M. D. J. Am. Chem. Soc. 1957, 79, 1920.
24. Cyclopentanone enolates have been shown to give high threo selectivity in their reactions with aldehydes and ketones: (a) Fellman, P.; Dubois, J.-E. Tetrahedron 1978, 34, 1349. (b) Dubois, J. E.; Dubois, M. J. Chem. Soc. Chem. Commun. 1968, 1567.
25. Cyclopentanone enolates have been shown to give high threo selectivity in their reactions with aldehydes and ketones: (a) Fellman, P.; Dubois, J.-E. Tetrahedron 1978, 34, 1349. (b) Dubois, J. E.; Dubois, M. J. Chem. Soc. Chem. Commun. 1968, 1567.
26. (a) Braun, M. In Stereoselective Synthesis; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Thieme: Stuttgart, 1996; Vol. 3, pp 1603-1607, and references therein.
27. (b) Majewski, M.; Gleave, D. M. Tetrahedron Lett. 1989, 30, 5681.
28. (c) Noyori, R.; Nishida, I.; Sakata, J. J. Am. Chem. Soc. 1983, 105, 1598.
29. (d) Heathcock, C. H.; Buse, C. T.; Kleschick, W. A.; Pirrung, M. C.; Sohn, J. E.; Lampe, J. J. Org. Chem. 1980, 45, 1066.
30. It is known that steric hindrance on the enolate favors the erythro/threo equilibration, probably due to the release of strain in the aldolate; see refs 10 and 15a.
31. Posner, G. H.; Lentz, C. M. J. Am, Chem. Soc. 1979, 101, 934.
32. Stereochemical assignment of 10d: The diastereotopic hydrogens attached to C-3 in ketone 2 appeared at δ 2.28 (dd, J = 17.9, 3.1 Hz) and 2.45 ppm (dd, J = 17.9, 8.5 Hz). The signal at lower field was assigned to the pro-S H-3 since its irradiation caused enhancement of H-2 (δ 3.76 ppm) and the other H-3 signal, while irradiation of the signal at δ 2.28 ppm (pro-R H-3) caused enhancement of only the other H-3 proton, H-2 being unaffected. In the deuterated ketone 10d, the signal at δ 2.45 ppm is not present and H-2 has a coupling constant of 2.9 Hz, typical of a trans arrangement, with the residual H-3 hydrogen (δ 2.20 ppm, bs).