Enamine catalysis is a powerful strategy for the catalytic generation and use of carbanion equivalents

Accounts of Chemical Research

Volumn 37, Issue 8, 2004, Pages 548-557

  List, Benjamin ^a,b  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

^b UNIVERSITY OF COLOGNE   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; BASE; ENAMINE; PROLINE;

ALDOL REACTION; AMINATION; ARTICLE; CATALYSIS; MANNICH REACTION; MICHAEL ADDITION; REACTION ANALYSIS; SYNTHESIS;

EID: 4143095871     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar0300571     Document Type: Article

References (54)

1. (a) Yoshikawa, N.; Kumagai, N.; Matsunaga, S.; Moll, G.; Ohshima, T.; Suzuki, T.; Shibasaki, M. Direct Catalytic Asymmetric Aldol Reaction: Synthesis of Either syn- or anti-α,β-Dihydroxy Ketones. J. Am. Chem. Soc. 2001, 123, 2466-2467.
2. (b) For the first direct catalytic asymmetric intermolecular aldol reaction, see: Yamada, Y. M. A.; Yoshikawa, N.; Sasai, H.; Shibsaki, M. Direct Catalytic Asymmetric Aldol Reaction of Aldehydes with Unmodified Ketones. Angew. Chem., Int. Ed. Engl. 1997, 36, 1871-1873.
3. Trost, B. M.; Yeh, V. S. C. A Dinuclear Zn Catalyst for the Asymmetric Nitroaldol (Henry) Reaction. Angew. Chem., Int. Ed. Engl. 2002, 41, 861-863.
4. Evans, D. A.; Nelson, S. G. Chiral Magnesium Bis(sulfonamide) Complexes as Catalysts for the Merged Enolization and Enantioselective Amination of N-Acyloxazolidinones. A Catalytic Approach to the Synthesis of Arylglycins. J. Am. Chem. Soc. 1997, 119, 6452-6453.
5. Anand, N. K.; Carreira, E. M. A Simple, Mild, Catalytic, Enantioselective Addition of Terminal Acetylenes to Aldehydes. J. Am. Chem. Soc. 2001, 123, 9687-9688.
6. Ito, Y.; Sawamura, M.; Hayashi, T. Catalytic Asymmetric Aldol Reaction: Reaction of Aldehydes with Isocyanoacetate Catalyzed by a Chiral Ferrocenylphosphine-Gold(I) Complex. J. Am. Chem. Soc. 1986, 108, 6405-6406.
7. 2- Symmetric Chiral Quaternary Ammonium Bromides as Novel Chiral Phase-Transfer Catalysts: Synthesis and Application to Practical Asymmetric Synthesis of α-Amino Acids. J. Am. Chem. Soc. 2003, 125, 5139-5151.
8. Spielvogel, D. J.; Buchwald, S. L. Nickel-BINAP Catalyzed Enantioselective α-Arylation of α-Substituted γ- Butyrolactones. J. Am. Chem. Soc. 2002, 124, 3500-3501.
9. Basavaiah, D.; Rao, A. J.; Satyanarayana, T. Recent Advances in the Baylis-Hillman Reaction and Applications. Chem. Rev. 2003, 103, 811-891.
10. For a recent example, see: Shah, M. H.; France, S.; Lectna, T. Bicarbonate Salts as Cost-Effective Bases for the Synthesis of Ketenes and Their Synthetic Equivalents Applied to the Asymmetric Synthesis of β-Lactams. Synlett 2003, 1937-1939.
11. For overviews, see: (a) List, B. Asymmetric Aminocatalysis. Synlett 2001, 1675-1686.
12. (b) List, B. Proline-Catalyzed Asymmetric Reactions. Tetrahedron 2002, 58, 5573-5590.
13. Stork, G.; Brizzolara, A.; Landesman, H.; Szmuszkovicz, J.; Terrell, R. The Enamine Alkylation and Acylation of Carbonyl Compounds. J. Am. Chem. Soc. 1963, 85, 207-222.
14. For a nice review on the catalytic asymmetric aldol reaction, including the use of aldolase enzymes, see: Machajewski, T. D.; Wong, C.-H. The Catalytic Asymmetric Aldol Reaction. Angew. Chem., Int. Ed. Engl. 2000, 39, 1352-1375.
15. See, for example: (a) Barbas, C. F., III; Heine, A.; Zhong, G.; Hoffmann, T.; Gramatikova, S.; Bioernstedt, R.; List, B.; Anderson, J.; Stura, E. A.; Wilson, I.; Lerner, R. A. Immune vs. Natural Selection: Antibody Aldolases with Enzymic Rates but Broader Scope. Science 1997, 278, 2085-2092.
16. (b) Turner, J.; Bui, T.; Lerner, R. A.; Barbas, C. F., III; List, B. An Efficient Benchtop System for Multigram-Scale Kinetic Resolutions Using Aldolase Antibodies. Chem. Eur. J. 2000, 6, 2772-2774.
17. Hajos, Z. G.; Parrish, D. R. Asymmetric Synthesis of Bicyclic Intermediates of Natural Product Chemistry. J. Org. Chem. 1974, 39, 1615-1621.
18. (b) Eder, U.; Sauer, G.; Wiechert, R. New Type of Asymmetric Cyclization to Optically Active Steroid CD Partial Structures. Angem Chem., Int. Ed. Engl. 1971, 10, 496-497.
19. List, B.; Lerner, R. A.; Barbas, C. F., III Proline-Catalyzed Direct Asymmetric Aldol Reactions. J. Am. Chem. Soc. 2000, 122, 2395-2396.
20. (b) Notz, W.; List, B. Catalytic Asymmetric Synthesis of anti-1,2-diols. J. Am. Chem. Soc. 2000, 122, 7386-7387.
21. (c) List, B.; Pojarliev, P.; Castello, C. Proline-Catalyzed Asymmetric Aldol Reactions between Ketones and α-Unsubstituted Aldehydes. Org. Lett. 2001, 3, 573-575.
22. Northrup, A. B.; MacMillan, D. W. C. The First Direct and Enantioselective Cross-Aldol Reaction of Aldehydes. J. Am. Chem. Soc. 2002, 124, 6798-6799.
23. Pihko, P. M.; Erkkilä, A. Enantioselective synthesis of prelactone B using a proline-catalyzed crossed-aldol reaction. Tetrahedron Lett. 2003, 44, 7607-7609.
24. Dias, L. C.; Steil, L. J.; Vasconcelos, V. de A. A short and efficient synthesis of (+)-prelactone B. Tetrahedron: Asymmetry 2004, 15, 147-150.
25. Pidathala, C.; Hoang, L.; Vignola, N.; List, B. Direct Catalytic Asymmetric Enolexo-Aldolizations. Angem Chem., Int. Ed. Engl. 2003, 42, 2785-2788.
26. Bahmanyar, S.; Houk, K. N. The Origin of Stereoselectivity in Proline-Catalyzed Intramolecular Aldol Reactions. J. Am. Chem. Soc. 2001, 123, 9922-9923.
27. (b) Bahmanyar, S.; Houk, K. N. Transition States of Amine-Catalyzed Aldol Reactions Involving Enamine Intermediates: Theoretical Studies of Mechanism, Reactivity, and Stereoselectivity. J. Am. Chem. Soc. 2001, 123, 11273-11283. Also see: Bahmanyar, S.; Houk, K. N.; Martin, H. J.; List, B. Quantum Mechanical Predictions of the Stereoselectivities of Proline-Catalyzed Asymmetric Intermolecular Aldol Reactions. J. Am. Chem. Soc. 2003, 125, 2475-2479.
28. (b) Bahmanyar, S.; Houk, K. N. Transition States of Amine-Catalyzed Aldol Reactions Involving Enamine Intermediates: Theoretical Studies of Mechanism, Reactivity, and Stereoselectivity. J. Am. Chem. Soc. 2001, 123, 11273-11283. Also see: Bahmanyar, S.; Houk, K. N.; Martin, H. J.; List, B. Quantum Mechanical Predictions of the Stereoselectivities of Proline-Catalyzed Asymmetric Intermolecular Aldol Reactions. J. Am. Chem. Soc. 2003, 125, 2475-2479.
29. See, for example: Agami, C. Mechanism of the proline-catalyzed Enantioselective Aldol Reaction, Recent Advances. Bull. Soc. Chim. Fr. 1988, 3, 499-507.
30. Hoang, L.; Bahmanyar, S.; Houk, K. N.; List, B. Kinetic and Stereochemical Evidence for the Involvement of Only One Proline Molecule in the Transition States of Proline-Catalyzed Intra- and Intermolecular Aldol Reactions. J. Am. Chem. Soc 2003, 125, 16-17.
31. List, B.; Hoang, L.; Martin, H. J. New Mechanistic Studies on the Proline-Catalyzed Aldol Reaction. Proc. Natl. Acad. Sci. 2004, 101, 5839-5842.
32. 2O. Tetrahedron Lett. 1999, 40, 307-310.
33. List, B. The Direct Catalytic Asymmetric Three-Component Mannich Reaction. J. Am. Chem. Soc. 2000, 122, 9336-9337.
34. (b) List, B.; Pojarliev, P.; Biller, W. T.; Martin, H. J. The Proline-Catalyzed Direct Asymmetric Three-Component Mannich Reaction: Scope, Optimization, and Application to the Highly Enantioselactive Synthesis of 1,2-Amino Alcohols. J. Am. Chem. Soc. 2002, 124, 827-833.
35. Highly Enantioselective Synthesis of 1,2-Amino Alcohol Derivatives via Proline-Catalyzed Mannich Reaction. Pojarliev, P.; Biller, W. T.; Martin, H. J.; List, B. Synlett 2003, 1903-1904.
36. Bahmanyar, S.; Houk, K. N. Origins of Opposite Absolute Stereoselectivities in Proline-Catalyzed Direct Mannich and Aldol Reactions. Org. Lett. 2002, 5, 1249-1251.
37. List, B.; Pojarliev, P.; Martin, H. J. Efficient Proline-Catalyzed Michael-Additions of Unmodified Ketones to Nitroolefins. Org. Lett. 2001, 3, 2423-2425.
38. (b) Also see: A Novel Proline-Catalyzed Three-Component Reaction of Ketones, Aldehydes, and Meldrum's Acid. List, B.; Castello, C. Synlett 2001, 1687-1689.
39. Enders, D.; Seki, A. Proline-Catalyzed Enantioselective Michael Additions of Ketones to Nitrostyrene. Synlett 2002, 26-28.
40. (b) Betancort, J. M.; Sakthivel, K.; Thayumanavan, R.; Barbas, C. F., III Catalytic enantioselective direct Michael additions of ketones to alkylidene malonates. Tetrahedron Lett. 2001, 42, 4441-4444.
41. (c) Alexakis, A.; Andrey, O. Diamine-Catalyzed Asymmetric Michael Additions of Aldehydes and Ketones to Nitrostyrene. Org. Lett. 2002, 4, 3611-3614.
42. List, B. Direct Asymmetric α-Amination of Aldehydes J. Am. Chem. Soc. 2002, 124, 5656-5657.
43. Hagiwara, H.; Okabe, T.; Hakoda, K.; Hoshi, T.; Ono, H.; Kamat, V. P.; Suzuki, T.; Ando, M. Catalytic enamine reaction: an expedient 1,4-conjugate addition of naked aldehydes to vinyl ketones and its application to synthesis of cyclohexenone from Stevia purpurea. Tetrahedron Lett. 2001, 42, 2705-2707.
44. (b) Bøgevig, A.; Kumaragurubaran, N.; Jørgensen, K. A. Direct catalytic asymmetric aldol reactions of aldehydes. Chem. Commun. 2002, 620-621.
45. (c) Betancort, J. M.; Barbas, C. F., III Catalytic Direct Asymmetric Michael Reactions: Taming Naked Aldehyde Donors. Org. Lett. 2001, 3, 3737-3740.
46. Bøgevig, A.; Juhi, K.; Kumaragurubaran, N.; Zhuang, W.; Jørgensen, K. A. Direct Organo-Catalytic Asymmetric α-Amination of Aldehydes - A Simple Approach to Optically Active α-Amino Aldehydes, α-Amino Alcohols, and α-Amino Acids. Angew. Chem., Int. Ed. Engl. 2002, 41, 1790-1793.
47. List, B. et al. Manuscript in preparation.
48. Meyers, A. I.; Williams, D. R.; Erickson, G. W.; White, S.; Druelinger, M., Enantioselective alkylation of ketones via chiral, nonracemic lithioenamines. An asymmetric synthesis of α-alkyl and α,α′-dialkyl cyclic ketones. J. Am. Chem. Soc. 1981, 103, 3081-3087.
49. (b) Evans, D. A. Stereoselective Alkylation Reactions of Chiral Metal Enolates. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1983; Vol. 3, Chapter 1, p 1.
50. (c) Job, A.; Janeck, C. F.; Bettray, W.; Peters, R.; Enders, D. The SAMP-/RAMP-hydrazone methodology in asymmetric synthesis. Tetrahedron 2002, 58, 2253-2329.
51. Maruoka, K.; Ooi, T. Enantioselective Amino Acid Synthesis by Chiral Phase-Transfer Catalysis. Chem. Rev. 2003, 103, 3013-3028.
52. Vignola, N.; List, B. Catalytic Asymmetric Intramolecular α-Alkylation of Aldehydes. J. Am. Chem. Soc. 2004, 126, 450-451.
53. See, for example: Martin, H. J.; List, B. Mining Sequence Space for Asymmetric Aminocatalysis: N-Terminal Prolyl-Peptides Efficiently Catalyze Enantioselective Aldol and Michael Reactions. Synlett 2003, 1901-1902.
54. See, for example: Brown, S. P.; Brochu, M. P.; Sinz, C. J.; MacMillan, D. W. C. The Direct and Enantioselective Organocatalytic α-Oxidation of Aldehydes. J. Am. Chem. Soc, 2003, 125, 10808-10809.