Synthesis of pyroglutamic acid derivatives via double michael reactions of alkynones

Organic Letters

Volumn 9, Issue 11, 2007, Pages 2159-2162

  Scansetti, Myriam ^a   Hu, Xiangping ^a   McDermott, Benjamin P ^b   Lam, Hon Wai ^a  

^a UNIVERSITY OF EDINBURGH   (United Kingdom)

^b ASTRAZENECA   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 34250653256     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol070674f     Document Type: Article

References (34)

1. For a recent review, see: Nájera, C.; Yus, M. Tetrahedron: Asymmetry 1999, 10, 2245-2303.
2. For recent, representative examples, see: (a) Soloshonok, V. A.; Cai, C.; Yamada, T.; Ueki, H.; Ohfune, Y.; Hruby, V. J. J. Am. Chem. Soc. 2005, 127, 15296-15303.
3. (b) Chang, M.-Y.; Sun, P.-P.; Chen, S.-T.; Chang, N.-C. Tetrahedron Lett. 2003, 44, 5271-5273.
4. (c) Alvarez-Ibarra, C.; Csáky, A. G.; Gómez de la Olivia, C. Eur. J. Org. Chem. 2002, 4190-4194.
5. (d) Merino, P.; Revuelta, J.; Tejero, T.; Chiacchio, U.; Rescifina, A.; Piperno, A.; Romeo, G. Tetrahedron: Asymmetry 2002, 13, 167-172.
6. Little, R. D.; Masjedizadeh, M. R.; Wallquist, O.; McLoughlin, J. I. Org. React. 1995, 47, 315-512.
7. (a) Grossman, R. B.; Varner, M. A.; Skaggs, A. J. J. Org. Chem. 1999, 64, 340-341.
8. (b) Grossman, R. B.; Rasne, R. M.; Patrick, B. O. J. Org. Chem. 1999, 64, 7173-7177.
9. (c) Grossman, R. B.; Pendharker, D. S.; Patrick, B. O. J. Org. Chem. 1999, 64, 7178-7183.
10. (d) Grossman, R. B.; Skaggs, A. J.; Kray, A. E.; Patrick, B. O. Org. Lett. 1999, 1, 1583-1586.
11. (e) Grossman, R. B.; Pendharker, D. S.; Rasne, R. M.; Varner, M. A. J. Org. Chem. 2000, 65, 3255-3258.
12. (f) Grossman, R. B.; Rasne, R. M. Org. Lett. 2001, 3, 4027-4030.
13. (g) Holeman, D. S.; Rasne, R. M. Grossman, R. B. J. Org. Chem. 2002, 67, 3149-3151.
14. (h) Hattori, K. Grossman, R. B. J. Org. Chem. 2003, 68, 1409-1417. For a review, see
15. (i) Grossman, R. B. Synlett 2001, 13-21.
16. Hughes, F., Jr.; Grossman, R. B. Org. Lett. 2001, 3, 2911-2914.
17. For a review of transition-metal-catalyzed Michael reactions of 1,3-dicarbonyl compounds, see: Christoffers, J. Eur. J. Org. Chem. 1998, 1259-1266.
18. For examples of iron-catalyzed Michael reactions of 1,3-dicarbonyl compounds, see: (a) Fei, C. P.; Chan, T. H. Synthesis 1982, 467-468.
19. (b) Kočovksý, P.; Dvořák, D. Tetrahedron. Lett. 1986, 27, 5015-5108.
20. (c) Christoffers, J. Chem. Commun. 1997, 943-944.
21. (d) Christoffers, J. J. Chem. Soc., Perkin Trans. 1 1997, 3141-3149.
22. (e) Christoffers, J. Synlett 2001, 723-732.
23. For examples of zinc-catalyzed Michael reactions of 1,3-dicarbonyl compounds, see: Brunner, H.; Krumey, C. J. Mol. Catal. A 1999, 142, 7-15.
24. For examples of magnesium-catalyzed Michael reactions of 1,3-dicarbonyl compounds, see: (a) Ji, J.; Barnes, D. M.; Zhang, J.; King, S. A.; Wittenberger, S. J.; Morton, H. E. J. Am. Chem. Soc. 1999, 121, 10215-10216.
25. (b) Barnes, D. M.; Ji, J.; Fickes, M. G.; Fitzgerald, M. A.; King, S. A.; Morton, H. E.; Plagge, F. A.; Preskill, M.; Wagaw, S. H.; Wittenberger, S. J.: Zhang, J. J. Am. Chem. Soc. 2002, 124, 13097-13105.
26. (c) MacCulloch, A. C.; Yolka, S.; Jackson, R. F. W. Synlett 2002, 1700-1702.
27. For examples of nickel-catalyzed Michael reactions of 1,3-dicarbonyl compounds, see: (a) Nelson, J. H.; Howells, P. N.; DeLullo, G. C.; Landen, G. L.; Henry, R. A. J. Org. Chem. 1980, 45, 1246-1249.
28. (b) Clariana, J.; Gálvez, N.; Marchi, C.; Moreno-Mañas, M.; Vallribera, A.; Molins, E. Tetrahedron 1999, 55, 7331-7344.
29. (c) Christoffers, J.; Rößler, U.; Werner, T. Eur. J. Org. Chem. 2000, 701-705.
30. (d) Evans, D. A.; Seidel, D. J. Am. Chem. Soc. 2005, 127, 9958-9959.
31. (e) Evans, D. A.; Thomson, R. J.; Franco, F. J. Am. Chem. Soc. 2005, 127, 10816-10817.
32. (f) Itoh, K.; Hasegawa, M.; Tanaka, J.; Kanemasa, S. Org. Lett. 2005, 7, 979-981.
33. (g) Yanagita, H.; Kodama, K.; Kanemasa, S. Tetrahedron Lett. 2006, 47, 9353-9357.
34. Tentative relative stereochemical assignment. NOESY spectra proved inconclusive in establishing the relative stereochemistry of 21.