Rational design of highly diastereoselective, organic base-catalyzed, room-temperature Michael addition reactions

Journal of Organic Chemistry

Volumn 65, Issue 20, 2000, Pages 6688-6696

  Soloshonok, Vadim A ^a   Cai, Chaozhong ^a   Hruby, Victor J ^a   Van Meervelt, Luc ^b   Yamazaki, Takashi ^c  

^a University of Arizona   (United States)

^b UNIVERSITY OF LEUVEN   (Belgium)

^c TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETOPHENONE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; GLYCINE; NICKEL COMPLEX; OXAZOLIDINONE DERIVATIVE; PYROGLUTAMIC ACID DERIVATIVE; SCHIFF BASE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; DECOMPOSITION; ELECTRON TRANSPORT; REACTION ANALYSIS; STEREOCHEMISTRY; STEREOMETRY; STRUCTURE ANALYSIS; TEMPERATURE;

CATALYSIS; ELECTRONS; GLYCINE; MAGNETIC RESONANCE SPECTROSCOPY; PYRROLIDONECARBOXYLIC ACID; SCHIFF BASES; STEREOISOMERISM; SUPPORT, U.S. GOV'T, P.H.S.; X-RAY DIFFRACTION;

EID: 0034613131     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0008791     Document Type: Article

References (63)

1. Stereochemically Defined C-Substituted Glutamic Acids and Their Derivatives. 7. For previous papers, see: (a) Soloshonok, V. A.; Cai, C.; Hruby, V. J.; Meervelt, L. V.; Mischenko, N. Tetrahedron 1999, 55, 12031. (b) Soloshonok, V. A.; Cai, C.; Hruby, V. J.; Meervelt, L. V. Tetrahedron 1999, 55, 12045. (c) Soloshonok, V. A.; Cai, C.; Hruby, V. J. Tetrahedron: Asymmetry 1999, 10, 4265. (d) Soloshonok, V. A.; Cai, C.; Hruby, V. J. Tetrahedron Lett. 2000, 41, 135. (e) Soloshonok, V. A.; Cai, C.; Hruby, V. J. Angew. Chem., Int. Ed. Engl. 2000, 39, 2172. (f) Soloshonok, V. A.; Cai, C.; Hruby, V. J. Organic Lett. 2000, 2, 747.
2. Stereochemically Defined C-Substituted Glutamic Acids and Their Derivatives. 7. For previous papers, see: (a) Soloshonok, V. A.; Cai, C.; Hruby, V. J.; Meervelt, L. V.; Mischenko, N. Tetrahedron 1999, 55, 12031. (b) Soloshonok, V. A.; Cai, C.; Hruby, V. J.; Meervelt, L. V. Tetrahedron 1999, 55, 12045. (c) Soloshonok, V. A.; Cai, C.; Hruby, V. J. Tetrahedron: Asymmetry 1999, 10, 4265. (d) Soloshonok, V. A.; Cai, C.; Hruby, V. J. Tetrahedron Lett. 2000, 41, 135. (e) Soloshonok, V. A.; Cai, C.; Hruby, V. J. Angew. Chem., Int. Ed. Engl. 2000, 39, 2172. (f) Soloshonok, V. A.; Cai, C.; Hruby, V. J. Organic Lett. 2000, 2, 747.
3. Stereochemically Defined C-Substituted Glutamic Acids and Their Derivatives. 7. For previous papers, see: (a) Soloshonok, V. A.; Cai, C.; Hruby, V. J.; Meervelt, L. V.; Mischenko, N. Tetrahedron 1999, 55, 12031. (b) Soloshonok, V. A.; Cai, C.; Hruby, V. J.; Meervelt, L. V. Tetrahedron 1999, 55, 12045. (c) Soloshonok, V. A.; Cai, C.; Hruby, V. J. Tetrahedron: Asymmetry 1999, 10, 4265. (d) Soloshonok, V. A.; Cai, C.; Hruby, V. J. Tetrahedron Lett. 2000, 41, 135. (e) Soloshonok, V. A.; Cai, C.; Hruby, V. J. Angew. Chem., Int. Ed. Engl. 2000, 39, 2172. (f) Soloshonok, V. A.; Cai, C.; Hruby, V. J. Organic Lett. 2000, 2, 747.
4. Stereochemically Defined C-Substituted Glutamic Acids and Their Derivatives. 7. For previous papers, see: (a) Soloshonok, V. A.; Cai, C.; Hruby, V. J.; Meervelt, L. V.; Mischenko, N. Tetrahedron 1999, 55, 12031. (b) Soloshonok, V. A.; Cai, C.; Hruby, V. J.; Meervelt, L. V. Tetrahedron 1999, 55, 12045. (c) Soloshonok, V. A.; Cai, C.; Hruby, V. J. Tetrahedron: Asymmetry 1999, 10, 4265. (d) Soloshonok, V. A.; Cai, C.; Hruby, V. J. Tetrahedron Lett. 2000, 41, 135. (e) Soloshonok, V. A.; Cai, C.; Hruby, V. J. Angew. Chem., Int. Ed. Engl. 2000, 39, 2172. (f) Soloshonok, V. A.; Cai, C.; Hruby, V. J. Organic Lett. 2000, 2, 747.
5. Stereochemically Defined C-Substituted Glutamic Acids and Their Derivatives. 7. For previous papers, see: (a) Soloshonok, V. A.; Cai, C.; Hruby, V. J.; Meervelt, L. V.; Mischenko, N. Tetrahedron 1999, 55, 12031. (b) Soloshonok, V. A.; Cai, C.; Hruby, V. J.; Meervelt, L. V. Tetrahedron 1999, 55, 12045. (c) Soloshonok, V. A.; Cai, C.; Hruby, V. J. Tetrahedron: Asymmetry 1999, 10, 4265. (d) Soloshonok, V. A.; Cai, C.; Hruby, V. J. Tetrahedron Lett. 2000, 41, 135. (e) Soloshonok, V. A.; Cai, C.; Hruby, V. J. Angew. Chem., Int. Ed. Engl. 2000, 39, 2172. (f) Soloshonok, V. A.; Cai, C.; Hruby, V. J. Organic Lett. 2000, 2, 747.
6. Stereochemically Defined C-Substituted Glutamic Acids and Their Derivatives. 7. For previous papers, see: (a) Soloshonok, V. A.; Cai, C.; Hruby, V. J.; Meervelt, L. V.; Mischenko, N. Tetrahedron 1999, 55, 12031. (b) Soloshonok, V. A.; Cai, C.; Hruby, V. J.; Meervelt, L. V. Tetrahedron 1999, 55, 12045. (c) Soloshonok, V. A.; Cai, C.; Hruby, V. J. Tetrahedron: Asymmetry 1999, 10, 4265. (d) Soloshonok, V. A.; Cai, C.; Hruby, V. J. Tetrahedron Lett. 2000, 41, 135. (e) Soloshonok, V. A.; Cai, C.; Hruby, V. J. Angew. Chem., Int. Ed. Engl. 2000, 39, 2172. (f) Soloshonok, V. A.; Cai, C.; Hruby, V. J. Organic Lett. 2000, 2, 747.
7. (a) Oare, D. A.; Heathcock, C. H. In Topics in Stereochemistry; Eliel, E. L., Wilen, S. H., Eds.; Wiley: New York, 1990; Vol. 19, pp 227-407.
8. (b) Oare, D. A.; Henderson, M. A.; Sanner, M. A.; Heathcock, C. H. J. Org. Chem. 1990, 55, 132.
9. For reviews on asymmetric synthesis of α-amino acids in general and the target amino acids in particular, see: (a) Duthaler, R. O. Tetrahedron 1994, 50, 1539. (b) Williams, R. M. Synthesis of Optically Active α-Amino Acids; Pergamon Press: Oxford, 1989.
10. For reviews on asymmetric synthesis of α-amino acids in general and the target amino acids in particular, see: (a) Duthaler, R. O. Tetrahedron 1994, 50, 1539. (b) Williams, R. M. Synthesis of Optically Active α-Amino Acids; Pergamon Press: Oxford, 1989.
11. For papers, see: (a) Kanemasa, S.; Tatsukawa, A.; Wada, E. J. Org. Chem. 1991, 56, 2875. (b) Schöllkopf, U.; Pettig, D.; Busse, U.; Egert, E.; Dyrbusch, M. Synthesis 1986, 737.
12. For papers, see: (a) Kanemasa, S.; Tatsukawa, A.; Wada, E. J. Org. Chem. 1991, 56, 2875. (b) Schöllkopf, U.; Pettig, D.; Busse, U.; Egert, E.; Dyrbusch, M. Synthesis 1986, 737.
13. For recent review on various synthetic transformations of pyroglutamic acid and its derivatives, see: Nájera, C.; Yus, M. Tetrahedron: Asymmetry 1999, 10, 2245.
14. (a) Hruby, V. J.; Sharma, S. D.; Collins, N.; Matsunaga, T. O.; Russell, K. C. In Synthetic Peptides: A User's Guide: Grant, G. A., Ed.; W. H. Freeman and Co., New York, 1992; pp 259-345.
15. (b) Hruby, V. J.; Qian, X. In Methods in Molecular Biology, Vol. 35, Peptide Synthesis and Purification Protocols; Pennington, M. W., Dunn, B. M., Eds.; Humana Press: Clifton, NJ, 1994; pp 201-240.
16. (a) Meraldi, J.-P.; Yamamoto, D.; Hruby, V. J.; Brewster, A. I. R. In Peptides: Chemistry, Structure and Biology; Walter, R., Meienhofer, J., Eds.; Ann Arbor Science Publishers: Ann Arbor, MI, 1975; pp 803-814.
17. (b) Meraldi, J.-P.; Hruby, V. J.; Brewster, A. I. R. Proc. Nat. Acad. Sci. U.S.A. 1977, 74, 1373.
18. (c) Hruby, V. J. In Perspectives in Peptide Chemistry; Eberle, A., Geiger, R., Wieland, T., Eds.; S. Karger: Basel, Switzerland, 1981; pp 207-220.
19. (d) Hruby, V. J. Life Sci. 1982, 37, 189.
20. For recent reviews on χ-constrained amino acids, see: (a) Hruby, V. J.; Li, G.; Haskell-Luevano, C.; Shenderovich, M. Biopolymers (Peptide Sci.) 1997, 43, 219. (b) Gibson, S. E.; Guillo, N.; Tozer, M. J. Tetrahedron 1999, 55, 585.
21. For recent reviews on χ-constrained amino acids, see: (a) Hruby, V. J.; Li, G.; Haskell-Luevano, C.; Shenderovich, M. Biopolymers (Peptide Sci.) 1997, 43, 219. (b) Gibson, S. E.; Guillo, N.; Tozer, M. J. Tetrahedron 1999, 55, 585.
22. Fan, W.; Boston, B. A.; Kesterson, R. A.; Hruby, V. J.; Cone, R. D. Nature 1997, 385, 165 and references therein.
23. (a) Ezquerra, J.; Pedregal, C.; Merino, I.; Flórez, J.; Barluenga, J.; García-Granda, S.; Llorca, M.-A. J. Org. Chem. 1999, 64, 6554.
24. (b) Seebach, D.; Hoffman, M. Eur. J. Org. Chem. 1998, 1337.
25. 11
26. (d) Antolini, L.; Forni, A.; Moretti, I.; Prati, F.; Laurent, E.; Gestmann, D. Tetrahedron: Asymmetry 1996, 7, 3309.
27. (e) Gestmann, D.; Laurent, A. J.; Laurent, E. G. J. Fluor. Chem. 1996, 80, 27.
28. (f) Hartzoulakis, B.; Gani, D. J. Chem. Soc., Perkin Trans. 1 1994, 2525.
29. (g) Suzuki, K.; Seebach, D. Liebigs Ann. Chem. 1992, 51.
30. (h) Belokon', Y. N.; Bulychev, A. G.; Pavlov, V. A.; Fedorova, E. B.; Tsyryapkin, V. A.; Bakhmutov, V. I.; Belikov, V. M. J. Chem. Soc., Perkin Trans. 1 1988, 2075.
31. (i) El Achqar, A.; Boumzebra, M.; Roumestant, M.-L.; Viallefont, P. Tetrahedron 1988, 44, 5319.
32. (j) Pettig, D.; Schöllkopf, U. Synthesis 1988, 173.
33. (k) Schöllkopf, U.; Pettig, D.; Schulze, E.; Klinge, M.; Egert, E.; Benecke, B.; Noltemeyer, M. Angew. Chem., Int. Ed. Engl. 1988, 27, 1194.
34. (l) Fitzi, R.; Seebach, D. Tetrahedron 1988, 44, 5277.
35. (m) Hartwig, W.; Born, L. J. Org. Chem. 1987, 52, 4352.
36. (n) Minowa, N.; Hirayama, M.; Fukatsu, S. Bull. Chem. Soc. Jpn. 1987, 60, 1761.
37. (o) Belokon', Y. N.; Bulychev, A. G.; Ryzhov, M. G.; Vitt, S. V.; Batsanov, A. S.; Struchkov, Y. T.; Bakhmutov, V. I.; Belikov, V. M. J. Chem. Soc., Perkin Trans. 1 1986, 1865.
38. Correction of the absolute configuration of products reported in the paper was made latter: Shibuya, A.; Sato, A.; Taguchi, T. Bioorg. Med. Chem. Lett. 1998, 8, 1979.
39. For short communications on some aspects of the results presented in this paper, see ref 1d.
40. For reviews, see: (a) Belokon', Y. N. Janssen Chim. Acta 1992, 70(2), 4. (b) Belokon', Y. N. Pure Appl. Chem. 1992, 64, 1917.
41. For reviews, see: (a) Belokon', Y. N. Janssen Chim. Acta 1992, 70(2), 4. (b) Belokon', Y. N. Pure Appl. Chem. 1992, 64, 1917.
42. Belokon', Y. N.; Kochetkov, K. A.; Churkina, T. D.; Ikonnikov, N. S.; Chesnokov, A. A.; Larionov, O. V.; Parmár, V. S.; Kumar, R.; Kagan, H. B. Tetrahedron: Asymmetry 1998, 9, 851.
43. For reviews, see: (a) Kukhar', V. P.; Resnati, G.; Soloshonok, V. A In Fluorine-Containing Amino Acids. Synthesis and Properties; Kukhar', V. P., Soloshonok, V. A., Eds.; John Wiley and Sons Ltd.: Chichester, 1994; Chapter 5. (b) Soloshonok, V. A. In Biomedical Frontiers of Fluorine Chemistry; Ojima, I., McCarthy, J. R., Welch, J. T., Eds.; ACS Books, American Chemical Society: Washington, D.C., 1996; Chapter 2. (c) Soloshonok, V. A. In Enantiocontrolled Synthesis of Fluoro-Organic Compounds: Stereochemical Challenges and Biomedicinal Targets; Soloshonok, V. A., Ed.; Wiley: Chichester, 1999; Chapter 7.
44. For reviews, see: (a) Kukhar', V. P.; Resnati, G.; Soloshonok, V. A In Fluorine-Containing Amino Acids. Synthesis and Properties; Kukhar', V. P., Soloshonok, V. A., Eds.; John Wiley and Sons Ltd.: Chichester, 1994; Chapter 5. (b) Soloshonok, V. A. In Biomedical Frontiers of Fluorine Chemistry; Ojima, I., McCarthy, J. R., Welch, J. T., Eds.; ACS Books, American Chemical Society: Washington, D.C., 1996; Chapter 2. (c) Soloshonok, V. A. In Enantiocontrolled Synthesis of Fluoro-Organic Compounds: Stereochemical Challenges and Biomedicinal Targets; Soloshonok, V. A., Ed.; Wiley: Chichester, 1999; Chapter 7.
45. For reviews, see: (a) Kukhar', V. P.; Resnati, G.; Soloshonok, V. A In Fluorine-Containing Amino Acids. Synthesis and Properties; Kukhar', V. P., Soloshonok, V. A., Eds.; John Wiley and Sons Ltd.: Chichester, 1994; Chapter 5. (b) Soloshonok, V. A. In Biomedical Frontiers of Fluorine Chemistry; Ojima, I., McCarthy, J. R., Welch, J. T., Eds.; ACS Books, American Chemical Society: Washington, D.C., 1996; Chapter 2. (c) Soloshonok, V. A. In Enantiocontrolled Synthesis of Fluoro-Organic Compounds: Stereochemical Challenges and Biomedicinal Targets; Soloshonok, V. A., Ed.; Wiley: Chichester, 1999; Chapter 7.
46. For successive papers, see: (a) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P.; Tararov, V. I.; Savel'eva, T. F.; Churkina, T. D.; Ikonnikov, N. S.; Kochetkov, K. A.; Orlova, S. A.; Pysarevsky, A. P.; Struchkov, Y. T.; Raevsky, N. I.; Belokon', Y. N. Tetrahedron: Asymmetry 1995, 6, 1741. (b) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P. Tetrahedron: Asymmetry 1996, 7, 1547. (c) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P. Tetrahedron 1996, 52, 12433. (d) Qiu, W.; Soloshonok, V. A.; Cai, C.; Tang, X.; Hruby, V. J., Tetrahedron 2000, 56, 2577.
47. For successive papers, see: (a) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P.; Tararov, V. I.; Savel'eva, T. F.; Churkina, T. D.; Ikonnikov, N. S.; Kochetkov, K. A.; Orlova, S. A.; Pysarevsky, A. P.; Struchkov, Y. T.; Raevsky, N. I.; Belokon', Y. N. Tetrahedron: Asymmetry 1995, 6, 1741. (b) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P. Tetrahedron: Asymmetry 1996, 7, 1547. (c) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P. Tetrahedron 1996, 52, 12433. (d) Qiu, W.; Soloshonok, V. A.; Cai, C.; Tang, X.; Hruby, V. J., Tetrahedron 2000, 56, 2577.
48. For successive papers, see: (a) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P.; Tararov, V. I.; Savel'eva, T. F.; Churkina, T. D.; Ikonnikov, N. S.; Kochetkov, K. A.; Orlova, S. A.; Pysarevsky, A. P.; Struchkov, Y. T.; Raevsky, N. I.; Belokon', Y. N. Tetrahedron: Asymmetry 1995, 6, 1741. (b) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P. Tetrahedron: Asymmetry 1996, 7, 1547. (c) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P. Tetrahedron 1996, 52, 12433. (d) Qiu, W.; Soloshonok, V. A.; Cai, C.; Tang, X.; Hruby, V. J., Tetrahedron 2000, 56, 2577.
49. For successive papers, see: (a) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P.; Tararov, V. I.; Savel'eva, T. F.; Churkina, T. D.; Ikonnikov, N. S.; Kochetkov, K. A.; Orlova, S. A.; Pysarevsky, A. P.; Struchkov, Y. T.; Raevsky, N. I.; Belokon', Y. N. Tetrahedron: Asymmetry 1995, 6, 1741. (b) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P. Tetrahedron: Asymmetry 1996, 7, 1547. (c) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P. Tetrahedron 1996, 52, 12433. (d) Qiu, W.; Soloshonok, V. A.; Cai, C.; Tang, X.; Hruby, V. J., Tetrahedron 2000, 56, 2577.
50. Electron donor-acceptor type attractive interactions between the nickel (II) ion and fluorine atoms, were shown to be a critical factor controlling virtually complete diastereoselectivity in the aldol addition reaction between trifluoroacetone and Ni(II) complex of the Schiff bases of glycine with (S)-o-[N-(N-benzylprolyl)amino]benzophenone (see ref 18).
51. Soloshonok, V. A.; Kukhar', V. P.; Galushko, S. V.; Svistunova, N. Y.; Avilov, D. V.; Kuz'mina, N. A.; Raevsky, N. I.; Struchkov, Y. T.; Pysarevsky, A. P.; Belokon', Y. N. J. Chem. Soc., Perkin Trans. 1 1993, 3143.
52. Apart from the perfect conformational/electronic properties of these compounds (see text), the ready availability of their chiral versions renders cyclic imides 3 and 4 particularly promising Michael acceptors.
53. Evans, D. A.; Chapman, K. T.; Bisaha, J. J. Am. Chem. Soc. 1988, 110, 1238.
54. (a) Bordwell, F. G. Acc. Chem. Res. 1988, 21, 456.
55. a table is available on the WWW-Home-Page of Professor David A. Evans' group: http://daeiris.harvard.edn//DavidEvans.html.
56. Evans, D. A.; Anderson, J. C.; Taylor, M. K. Tetrahedron Lett 1993, 34, 5563.
57. Soloshonok, V. A.; Cai, C.; Hruby, V. J., unpublished data.
58. Taking into account that the particular planar geometry of the Ni(II) complex 2 could be a reason for the failure of the additions with 5a,b, we studied the reactions of the acyclic and more flexible N-(diphenylmethylene)glycine ethyl ester with 5a,b (DMF, rt, DBU). The results were the same; no trace of the addition products was found. As one can assume, the planar geometry, like for instance in the case of 3 and 4, is the critical topographic requirement for TS of type A or B (Figure 4) to be formed.
59. The (2R*,3S*) relative stereochemistry for the aromatic (R = Ph) derivatives is a consequence of the Cahn-Ingold-Prelog priority (see ref 26) and is stereochemically equivalent to the (2R*,3R*) configuration in the aliphatic (R = Me) series of compounds.
60. Cahn, R. S.; Ingold, C.; Prelog, V. Angew. Chem., Int. Ed. Engl. 1966, 5, 385.
61. Analysis of the crude reaction mixture (NMR) showed that the content of the major diastereomer 7c-j was at least 97%, while the second diastereomer and/or byproducts was/were formed in an amount not greater than 3%.
62. Sheldrick, G. M. (1998) SHELXTL-Plus. Program for the Solution and Refinement of Crystal Structures. Bruker Analytical X-ray Systems, Madison, WI.
63. Spek, A. L. Acta Crystallogr. 1990, A46, C-34.