Manganese(III) acetate-mediated alkylation of β-keto esters and β-keto amides: An enantio- and diastereo-selective approach to substituted pyrrolidinones

Organic and Biomolecular Chemistry

Volumn 1, Issue 2, 2003, Pages 373-380

  Bar, Gregory ^a   Parsons, Andrew F ^a   Thomas, C Barry ^a  

^a UNIVERSITY OF YORK   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; ALKYLATION; CHEMICAL BONDS; COPPER COMPOUNDS; ESTERS; HEATING; MANGANESE COMPOUNDS; MOLECULAR DYNAMICS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOCHEMISTRY; SUBSTITUTION REACTIONS;

KETO AMIDES; KETO ESTERS; MANGANESE ACETATE; PYRROLIDINONES;

ORGANIC COMPOUNDS;

EID: 0041317245     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b209123b     Document Type: Article

References (46)

1. B. B. Snider, Chem. Rev., 1996, 96, 339.
2. T. Linker, J. Prakt. Chem., 1997, 339, 488.
3. (a) G. G. Melikyan, Aldrichimica Acta, 1998, 31, 50
4. (b) G. G. Melikyan, Organic Reactions, ed., L. A. Paquette, John Wiley, New York, 1997, 49, 427.
5. A. F. Parsons, An Introduction to Free Radical Chemistry, Blackwell Science, Oxford, 2000.
6. B. B. Snider and R. B. Smith, Tetrahedron, 2002, 58, 25.
7. J. Y. Nédélec and K. Nohair, Synlett, 1991, 659.
8. H. Nishino, S-I. Tategami, T. Yamada, J. D. Korp and K. Kurosawa, Bull. Chem. Soc. Jpn., 1991, 64, 1800.
9. E. I. Heiba and R. M. Dessau, J. Org. Chem., 1974, 39, 3456.
10. R. Lavilla, A. Spada, I. Carranco and J. Bosch, J. Org. Chem., 2001, 66, 1487.
11. R. Kumabe, H. Nishino, M. Yasutake, V.-H. Nguyen and K. Kurosawa, Tetrahedron Lett., 2001, 42, 69.
12. M. Allegretti, A. D'Annibale and C. Trogolo, Tetrahedron, 1993, 49, 10705.
13. G. Midgley and C. B. Thomas, J. Chem. Soc., Perkin Trans. 2, 1987, 1103.
14. G. Bar, A. F. Parsons and C. B. Thomas, Tetrahedron, 2001, 57, 4719.
15. P. C. Montevecchi and M. L. Navacchia, Tetrahedron, 2000, 56, 9339.
16. E. J. Corey and A. K. Ghosh, Chem. Lett., 1987, 223.
17. J. M. Mellor and S. Mohammed, Tetrahedron, 1993, 49, 7547.
18. J. M. Mellor and S. Mohammed, Tetrahedron, 1993, 49, 7557.
19. E. J. Corey and A. K. Ghosh, Tetrahedron Lett., 1987, 28, 175.
20. Part of this work has been reported as a preliminary communication: G. Bar, A. F. Parsons and C. B. Thomas, Synlett, 2002, 1069.
21. For related asymmetric manganese(III)-based approaches using chiral auxiliaries see: (a) F. Garzino, A. Méou and P. Brun, Tetrahedron Lett., 2000, 41, 9803
22. (b) B. B. Snider and Q. Zhang, Tetrahedron Lett., 1992, 33, 5921
23. (c) Q. Zhang, R. M. Mohan, L. Cook, S. Kazanis, D. Peisach, B. M. Foxman and B. B. Snider, J. Org. Chem., 1993, 58, 7640
24. (d) P. A. Zoretic, X. Weng, M. S. Biggers, M. L. Caspar and D. G. Davis, Tetrahedron Lett., 1992, 33, 2637
25. (e) R. Galeazzi, G. Mobbili and M. Orena, Tetrahedron, 1996, 54, 1069
26. (f) B. Cardillo, R. Galeazzi, G. Mobbili and M. Orena, Synlett, 1995, 1159
27. (g) R. Galeazzi, S. Geremia, G. Mobbili and M. Orena, Tetrahedron: Asymmetry, 1996, 7, 3573.
28. (a) M. G. Moloney, Nat. Prod. Rep., 1999, 16, 485
29. (b) P. W. H. Chan, I. F. Cottreli and M. G. Moloney, J. Chem. Soc., Perkin Trans. 1, 2001, 2997
30. (c) P. W. H. Chan, I. F. Cottrell and M. G. Moloney, J. Chem. Soc., Perkin Trans. 1, 2001, 3007
31. (d) J. E. Baldwin, A. M. Fryer and G. J. Pritchard, J. Org. Chem., 2001, 66, 2588
32. (e) A. Ali, V. U. Ahmad, B. Ziemer and J. Liebscher, Tetrahedron: Asymmetry, 2000, 11, 4365
33. (f) Y. Aoyagi and R. M. Williams, Tetrahedron, 1998, 54, 13045.
34. M. J. Beard, J. H. Bailey, D. T. Cherry, M. G. Moloney, S. B. Shim, K. A. Statham, M. J. Bamford and R. B. Lamont, Tetrahedron, 1996, 52, 3719.
35. It is interesting to note that a related intramolecular cyclisation of an α-methyl β-amido ester was unsuccessful: D. T. Davies, N. Kapur and A. F. Parsons, Tetrahedron Lett., 1998, 39, 4397.
36. In these types of compounds, the peaks for the two hydrogen atoms at C-4 are often well separated for each of the two diastereoisomers: J. Ezquerra, C. Pedregal, A. Rubio, B. Yruretagoyena, A. Escribano and F. Sánchez-Ferrando, Tetrahedron, 1993, 49, 8665.
37. (a) J. Iqbal, R. R. Srivastava and M. A. Khan, Tetrahedron Lett., 1990, 31, 1485
38. (b) V. Nair, J. Mathew and J. Prabhakaran, Chem. Soc. Rev., 1997, 127
39. (c) X.-P. Gu, N. Nishida, I. Ikeda and M. Okahara, J. Org. Chem., 1987, 52, 3192
40. (d) X.-P. Gu, T. Okuhara, I. Ikeda and M. Okahara. Synthesis, 1988, 535
41. (e) I. Ikeda, X.-P. Gu, T. Okuhara and M. Okahara, Synthesis, 1990, 32
42. (f) Y. Hori, T.-A. Mitsudo and Y. Watanabe, Tetrahedron Lett., 1986, 27, 5389.
43. P.-K. Chiu and M. P. Sammes, Tetrahedron, 1990, 46, 3439.
44. For an alternative approach to 1,4-dicarbonyl compounds from β-keto esters see: J. B. Brogan and C. K. Zercher, J. Org. Chem., 1997, 62, 6444.
45. L. J. Breña-Valle, R. C. Sánchez and R. Cruz-Almanza, Tetrahedron: Asymmetry, 1996, 7, 1019.
46. P. D. Williams, D. S. Perlow, L. S. Payne, M. K. Holloway, P. K. S. Siegl, T. W. Schorn, R. J. Lynch, J. J. Doyle, J. F. Strouse, G. P. Vlasuk, K. Hoogsteen, J. P. Springer, B. L. Bush, T. A. Halgren, A. D. Richards, J, Kay and D. F. Veber, J. Med. Chem., 1991, 34, 887.