α-imino esters: Versatile substrates for the catalytic, asymmetric synthesis of α- and β-amino acids and β-lactams

Accounts of Chemical Research

Volumn 36, Issue 1, 2003, Pages 10-19

  Taggi, Andrew E ^a   Hafez, Ahmed M ^a   Lectka, Thomas ^a  

^a JOHNS HOPKINS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA AMINO ACID; AMINO ACID; BETA AMINO ACID; BETA LACTAM; ESTER; ESTER DERIVATIVE; IMINO ACID; LACTAM;

ALKYLATION; ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; CHEMISTRY; REACTION ANALYSIS; STEREOCHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALKYLATION; AMINO ACIDS; BETA-LACTAMS; CATALYSIS; ESTERS; IMINO ACIDS; STEREOISOMERISM;

EID: 0037244819     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar020137p     Document Type: Article

References (66)

1. Recent Reviews of amino acid synthesis: (a) Bloch, R. Additions of Organometallic Reagents to C=N Bonds: Reactivity and Selectivity. Chem. Rev. 1998, 98, 1407-1438. (b) Williams, R. M. Synthesis of Optically Active α-Amino Acids; Pergammon: New York, 1989. (c) Duthaler, R. O. Recent Developments in the Stereoselective Synthesis of α-Amino Acids. Tetrahedron 1994, 50, 1539-1650. (d) Hegedus, L. Synthesis of Amino Acids and Peptides Using Chromium Carbene Complex Photochemistry. Acc. Chem. Res. 1995, 28, 299-305.
2. Recent Reviews of amino acid synthesis: (a) Bloch, R. Additions of Organometallic Reagents to C=N Bonds: Reactivity and Selectivity. Chem. Rev. 1998, 98, 1407-1438. (b) Williams, R. M. Synthesis of Optically Active α-Amino Acids; Pergammon: New York, 1989. (c) Duthaler, R. O. Recent Developments in the Stereoselective Synthesis of α-Amino Acids. Tetrahedron 1994, 50, 1539-1650. (d) Hegedus, L. Synthesis of Amino Acids and Peptides Using Chromium Carbene Complex Photochemistry. Acc. Chem. Res. 1995, 28, 299-305.
3. Recent Reviews of amino acid synthesis: (a) Bloch, R. Additions of Organometallic Reagents to C=N Bonds: Reactivity and Selectivity. Chem. Rev. 1998, 98, 1407-1438. (b) Williams, R. M. Synthesis of Optically Active α-Amino Acids; Pergammon: New York, 1989. (c) Duthaler, R. O. Recent Developments in the Stereoselective Synthesis of α-Amino Acids. Tetrahedron 1994, 50, 1539-1650. (d) Hegedus, L. Synthesis of Amino Acids and Peptides Using Chromium Carbene Complex Photochemistry. Acc. Chem. Res. 1995, 28, 299-305.
4. Recent Reviews of amino acid synthesis: (a) Bloch, R. Additions of Organometallic Reagents to C=N Bonds: Reactivity and Selectivity. Chem. Rev. 1998, 98, 1407-1438. (b) Williams, R. M. Synthesis of Optically Active α-Amino Acids; Pergammon: New York, 1989. (c) Duthaler, R. O. Recent Developments in the Stereoselective Synthesis of α-Amino Acids. Tetrahedron 1994, 50, 1539-1650. (d) Hegedus, L. Synthesis of Amino Acids and Peptides Using Chromium Carbene Complex Photochemistry. Acc. Chem. Res. 1995, 28, 299-305.
5. For representative examples of Lewis acid-catalyzed enantioselective imine alkylations, see: (a) Kobayashi, S.; Ishitiani, H. Catalytic Enantioselective Addition to Imines. Chem. Rev. 1999, 99, 1069-1094. (b) Fujii, A.; Hagiwara, E.; Sodeoka, M. Mechanism of Palladium Complex-Catalyzed Enantioselective Mannich-Type Reaction: Characterization of A Novel Binuclear Palladium Enolate Complex. J. Am. Chem. Soc. 1999, 121, 5450-5458. A proline-catalyzed asymmetric Mannich reaction has also been reported: (c) List, B. The Direct Catalytic Asymmetric Three-Component Mannich Reaction. J. Am. Chem. Soc. 2000, 122, 9336-9337.
6. For representative examples of Lewis acid-catalyzed enantioselective imine alkylations, see: (a) Kobayashi, S.; Ishitiani, H. Catalytic Enantioselective Addition to Imines. Chem. Rev. 1999, 99, 1069-1094. (b) Fujii, A.; Hagiwara, E.; Sodeoka, M. Mechanism of Palladium Complex-Catalyzed Enantioselective Mannich-Type Reaction: Characterization of A Novel Binuclear Palladium Enolate Complex. J. Am. Chem. Soc. 1999, 121, 5450-5458. A proline-catalyzed asymmetric Mannich reaction has also been reported: (c) List, B. The Direct Catalytic Asymmetric Three-Component Mannich Reaction. J. Am. Chem. Soc. 2000, 122, 9336-9337.
7. For representative examples of Lewis acid-catalyzed enantioselective imine alkylations, see: (a) Kobayashi, S.; Ishitiani, H. Catalytic Enantioselective Addition to Imines. Chem. Rev. 1999, 99, 1069-1094. (b) Fujii, A.; Hagiwara, E.; Sodeoka, M. Mechanism of Palladium Complex-Catalyzed Enantioselective Mannich-Type Reaction: Characterization of A Novel Binuclear Palladium Enolate Complex. J. Am. Chem. Soc. 1999, 121, 5450-5458. A proline-catalyzed asymmetric Mannich reaction has also been reported: (c) List, B. The Direct Catalytic Asymmetric Three-Component Mannich Reaction. J. Am. Chem. Soc. 2000, 122, 9336-9337.
8. (a) Gomez-Bengoa, E.; Heron, N. M.; Didiuk, M. T.; Luchaco, C. A.; Hoveyda, A. H. Ni-Catalyzed Asymmetric Addition of Grignard Reagents to Unsaturated Cyclic Acetals. The Influence of Added Phosphine on Enantioselectivity. J. Am. Chem. Soc. 1998, 120, 7649-7650. For a review of α-amidoalkylation reactions, see: (b) Zaugg, H. E. α-Amidoalkylation at Carbon: Recent Advances -Part I. Synthesis 1984, 85-110.
9. (a) Gomez-Bengoa, E.; Heron, N. M.; Didiuk, M. T.; Luchaco, C. A.; Hoveyda, A. H. Ni-Catalyzed Asymmetric Addition of Grignard Reagents to Unsaturated Cyclic Acetals. The Influence of Added Phosphine on Enantioselectivity. J. Am. Chem. Soc. 1998, 120, 7649-7650. For a review of α-amidoalkylation reactions, see: (b) Zaugg, H. E. α-Amidoalkylation at Carbon: Recent Advances -Part I. Synthesis 1984, 85-110.
10. Weinreb, S. M. N-Sulfonyl Imines - Useful Synthons in Stereo-selective Organic Synthesis. Top. Curr. Chem. 1997, 190, 131-184.
11. Borzilleri, R. M.; Weinreb, S. M. Imino Ene Reactions in Organic Synthesis. Synthesis 1995, 347-360.
12. (a) Mikami, K.; Yajima, T.; Kaneko, M. Asymmetric Imine-Ene Reactions. Amino Acids 1998, 14, 311-318.
13. (b) Mikami, K.; Kaneko, M.; Yajima, T. Asymmetric Imine-ene Reactions with Chiral Glyoxylate-Derived α-Imino Esters: An Efficient Route to Asymmetric Synthesis of α-Amino Acids. Tetrahedron Lett. 1993, 34, 4841-4842.
14. (a) Hamley, P.; Helmchen, G.; Holmes, A. B.; Marshall, D. R.; MacKinnon, J. W. M. Diastereoselctive Imino Ester Cycloadditions - Enantioselective Synthesis of Azabyclyclo[2.2.1]heptenes. J. Chem. Soc., Chem. Commun. 1992, 786-788.
15. (b) Heintzelman, G. R.; Weinreb, S. M.; Parvez, M. Imino Diels-Alder-Based Construction of a Piperidine A-Ring Unit for Total Synthesis of the Marine Hepatotoxin Cylindrospermopsin. J. Org. Chem. 1996, 61, 4594-4599.
16. (c) Edwards, M. L.; Matt, J. E.; Wenstrupl, D. L.; Kemper, C. A.; Persichetti, R. A.; Margolin, A. L. Synthesis and Enzymatic Resolution of a Carbocyclic Analogue of Ribofuranosylamine. Org. Prep. Proc. Int. 1996, 28, 193-202.
17. Baillarge, M.; Goffic, F. L. A Facile Procedure for the Synthesis of N-(Tosyl) Imino-2 Acetic-Acid Esters, Important Enophiles for the Direct Synthesis of Exotic Alpha-Amino-Acids. Synth. Comm. 1987, 17, 1603-1606.
18. (a) Borrione, E.; Prato, M.; Scorrano, G.; Stivanello, M.; Lucchini, V. J. Synthesis and Cycloaddition Reactions of Ethyl Glyoxylate Imines. Synthesis of Substituted Furo[3,2-c]quinolines and 7H-Indeno[2,1-c]quinolines. Heterocycl. Chem. 1998, 25, 1831-1835.
19. (b) Manhas, M. S.; Ghosh, M.; Bose, A. K. Studies on Lactams. Part 84. β-Lactams via α-, β-Unsaturated Acid Chlorides: Intermediates for Carbapenem Antibiotics. J. Org. Chem. 1990, 55, 575-580.
20. (a) Malassa, I.; Matthies, D. N-Acyl-(α-Imino Acid Derivatives. Synthesis of N-Acyl-α-Oxoaldimines Liebigs Ann. Chem. 1986, 1133-1139.
21. (b) Muenser, P.; Steglich, W. Synthesis of α-Amino Acids by Reaction of tert-Butyl N-(t-Butoxycarbonyl)iminoacetate With C-Nucleophiles. Synthesis 1987, 223-225.
22. In some cases, N-acyl imino esters can be isolated. Schmitt, M.; Bourguignon, J.; Barlin, G. B.; Davies, L. P. Imidazo[1,2-b]-pyridazines. XXIII Some 5-Deaza Analogues. Synthesis of some 2-Aryl-6-(Chloro, methoxy or unsubstituted)-3-(variously substituted)imidazo[1,2-a]pyridines and Their Affinity for Central and Mitochondrial Benzodiazepine Receptors. Aust. J. Chem. 1997, 50, 719-726.
23. (a) Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. Catalytic, Enantioselective Alkylation of α-Imino Esters Using Late Transition Metal Phosphine Complexes as Catalysts. J. Am. Chem. Soc. 1998, 120, 4548-4549.
24. (b) Ferraris, D.; Young, B.; Cox, C.; Dudding, T.; Drury, W. J., III.; Ryzhkov, L.; Taggi, A. E.; Lectka, T. Catalytic, Enantioselective Alkylation of α-Imino Esters: The Synthesis of Nonnatural α-Amino Acid Derivatives. J. Am. Chem. Soc. 2002, 124, 67-77.
25. (a) Hagiwara, E.; Fujii, A.; Sodeoka, M. Enantioselective Addition of Enol Silyl Ethers to Imines Catalyzed by Palladium Complexes: A Novel Way to Optically Active Acylalanine Derivatives J. Am. Chem. Soc. 1998, 120, 2474-2475.
26. (b) Fujii, A.; Sodeoka, M. Palladium Diaqua and Hydroxo Complexes with Polymer-supported BINAP Ligands and Their Use for Catalytic Enantioselective Reactions Tetrahedron Lett. 1999, 40, 8011-8014.
27. Kobayashi, S.; Matsubara, R.; Kitagawa, H. Catalytic, Asymmetric Mannich-Type Reactions of N-Acylimino Esters for Direct Formation of N-Acylated Amino Acid Derivatives. Efficient Synthesis of a Novel Inhibitor of Ceramide Trafficking, HPA-12. Org. Lett. 2002, 4, 143-145.
28. Kobayashi, S.; Hamada, T.; Manabe, K. The Catalytic Asymmetric Mannich-Type Reactions in Aqueous Media. J. Am. Chem. Soc. 2002, 124, 5640-5641.
29. Ferraris, D.; Dudding, T.; Young, B.; Drury, W. J., III.; Lectka, T. Catalytic, Enantioselective Alkylations of N,O-Acetals. J. Org. Chem. 1999, 64, 2168-2169.
30. 2. J. Org. Chem. 1998, 63, 6090-6091.
31. (a) Mukaiyama, T.; Kobayashi, S.; Tamura, M.; Sagawa, Y. An Efficient and Extremely Mild Catalyst System, Combined Use of Trityl Chloride and Tin(II) Chloride, in the Aldol and Michael Reactions. Chem. Lett. 1987, 491-494.
32. (b) Mukaiyama, T.; Kobayashi, S.; Murakami, M. An Efficient Method for the Preparation of Threo Cross-Aldols from Silyl Enol Ethers and Aldehydes Using Trityl Perchlorate as a Catalyst. Chem. Lett. 1985, 447-450.
33. (a) Drury, W. J., III.; Ferraris, D.; Cox, C.; Young, B.; Lectka, T. A Novel Synthesis of α-Amino Acid Derivatives through Catalytic, Enantioselective Ene Reactions of α-Imino Esters J. Am. Chem. Soc. 1998, 120, 11006-11007. After our report, Jørgensen published an imino ene reaction catalyzed by copper BINAP: (b) Yao, S.; Fang, X.; Jørgensen, K. A. Catalytic Enantioselective Ene Reactions of Imines: A Simple Approach for the Formation of Optically Active α-Amino Acids. J. Chem. Soc. Chem. Commun. 1998, 2547-2548.
34. (a) Drury, W. J., III.; Ferraris, D.; Cox, C.; Young, B.; Lectka, T. A Novel Synthesis of α-Amino Acid Derivatives through Catalytic, Enantioselective Ene Reactions of α-Imino Esters J. Am. Chem. Soc. 1998, 120, 11006-11007. After our report, Jørgensen published an imino ene reaction catalyzed by copper BINAP: (b) Yao, S.; Fang, X.; Jørgensen, K. A. Catalytic Enantioselective Ene Reactions of Imines: A Simple Approach for the Formation of Optically Active α-Amino Acids. J. Chem. Soc. Chem. Commun. 1998, 2547-2548.
35. Elder, A. M.; Rich, D. H. Two Syntheses of the 16- and 17- Membered DEF Ring Systems of Chloropeptin and Complestatin. Org Lett. 1999, 1, 1443-1446.
36. (a) Chen, G.-M.; Ramachandran, P. V.; Brown, H. C. The Critical Importance of Water in the Asymmetric Allylboration of N-Trimethylsilylbenzaldimines with B-Allyldiisopinocampheylborane. Angew. Chem., Int. Ed. Engl. 1999, 38, 825-826.
37. (b) Nakamura, H.; Nakamura, K.; Yamamoto, Y. Catalytic Asymmetric Allylation of Imines via Chiral Bis-π-allylpalladium Complexes. J. Am. Chem. Soc. 1998, 120, 4242-4243.
38. (c) Nakamura, K.; Nakamura, H.; Yamamoto, Y. Chiral π-Allylpalladium-Catalyzed Asymmetric Allylation of Imines: Replacement of Allylstannanes by Allylsilanes. J. Org. Chem. 1998, 64, 2614-2615.
39. (d) Yanagisawa, A.; Nakashima, H.; Ishiba, A.; Yamamoto, H. Catalytic Asymmetric Allylation of Aldehydes Using a Chiral Silver(I) Complex. J. Am. Chem. Soc. 1996, 118, 4723-4724.
40. Fang, X.; Johannsen, M.; Yao, S.; Gathergood, N.; Hazell, R. G.; Jørgensen, K. A. Catalytic Approach for the Formation of Optically Active Allyl α-Amino Acids by Addition of Allylic Metal Compounds to α-Imino Esters. J. Org. Chem. 1999, 64, 4844-4849.
41. Saaby, A.; Fang, X.; Gathergood, N.; Jørgensen, K. A. Formation of Optically Active Aromatic α-Amino Acids by Catalytic Enantioselective Addition of Imines to Aromatic Compounds. Angew. Chem., Int. Ed. Engl. 2000, 39, 4114-4115.
42. Juhl, K.; Gathergood, N.; Jørgensen, K. A. Catalytic Asymmetric Direct Mannich Reactions of Carbonyl Compounds with α-Imino Esters. Angew. Chem., Int. Ed. Engl. 2001, 40, 2995-2997.
43. Knudsen, K. R.; Risgaard, T.; Nishiwaki, N.; Gothelf, K. V.; Jørgensen, K. A. The First Catalytic Asymmetric Aza-Henry Reaction of Nitronates with Imines: A Novel Approach to Optically Active β-Nitro-α-Amino Acid- and α,β-Diamino Acid Derivatives. J. Am. Chem. Soc. 2001, 123, 5843-5844.
44. Nishiwaki, N.; Knudsen, K. R.; Gothelf, K. V.; Jørgensen, K. A. Catalytic Enantioselective Addition of Nitro Compounds to Imines - A Simple Approach for the Synthesis of Optically Active β-Nitro-α-Amino Esters. Angew. Chem., Int. Ed. Engl. 2001, 40, 2992-2995.
45. Yao, S.; Saaby, S.; Hazell, R. G.; Jørgensen, K. A. Catalytic Enantioselective Aza-Diels-Alder Reactions of Imines- An Approach to Optically Active Nonproteinogenic α-Amino Acids. Chem. Eur. J. 2000, 6, 2435-2448.
46. Sodeoka et al. also investigated N-tosyl imine 1a with their catalysts and found the reaction proceeded with a high background rate leading to racemic products. See ref 2b.
47. Cordova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, C. F., III. A Highly Enantioselective Amino Acid-Catalyzed Route to Functionalized α-Amino Acids. J. Am. Chem. Soc. 2002, 124, 1842-1843.
48. (a) Taggi, A. E.; Hafez, A. M.; Wack, H.; Young, B.; Drury, W. J., III.; Lectka, T. Catalytic, Asymmetric Synthesis of β-Lactams. J. Am. Chem. Soc. 2000, 122, 7831-7832.
49. (b) Taggi, A. E.; Hafez, A. M.; Wack, H.; Young, B.; Ferraris, D.; Lectka, T. The Development of the First Catalyzed Reaction of Ketenes and Imines: Catalytic, Asymmetric Synthesis of β-Lactams. J. Am. Chem. Soc. 2002, 124, 6626-6635.
50. (a) Davoli, P.; Moretti, I.; Prati, F.; Alper, H. Carbonylation of Silylated Hydroxymethyl Aziridines to β-Lactams. J. Org. Chem. 1999, 64, 518-521.
51. (b) Fujieda, H.; Kanai, M.; Kambara, A. I.; Tomioka, K. A Ternary Complex Reagent for an Asymmetric Reaction of Lithium Ester Enolates with Imines. J. Am. Chem. Soc. 1997, 119, 2060-2061.
52. (c) Doyle, M. P.; Kalinin, A. V. Highly Enantioselective Route to β-Lactams via Intramolecular C-H Insertion Reactions of Diazoacetylazacycloalkanes Catalyzed by Chiral Dirhodium(II) Carboxamidates. Synlett 1995, 10, 1075-1076.
53. (a) Wilmouth, R. C.; Kassamally, S.; Westwood, N. J.; Sheppard, R. J.; Claridge, T. D. W.; Aplin, R. T.; Wright, P. A.; Pritchard, G. J.; Schofield, C. J. Mechanistic Insights into the Inhibition of Serine Proteases by Monocyclic Lactams. Biochemistry 1999, 38, 7989-7998.
54. (b) Taylor, P.; Anderson, V.; Dowden, J.; Flitsch, S. L.; Turner, N. J.; Loughran, K.; Walkinshaw, M. D. Novel Mechanism of Inhibition of Elastase by beta-Lactams Is Defined by Two Inhibitor Crystal Complexes. J. Biol. Chem. 1999, 274, 24901-24905.
55. Wack, H.; Drury, W. J., III.; Taggi, A. E.; Ferraris, D.; Lectka, T. Nucleophilic Metal Complexes as Acylation Catalysts: Solvent-Dependent 'Switch' Mechanisms Leading to the First Catalyzed Staudinger Reaction. Org. Lett. 1999, 1, 1985-1988.
56. Hodous, B. L.; Fu, G. C. Enantioselective Staudinger Synthesis of β-Lactams Catalyzed by a Planar-Chiral Nucleophile. J. Am. Chem. Soc. 2002, 124, 1578-1579.
57. (a) Hafez, A. M.; Taggi, A. E.; Wack, H.; Esterbrook, J.; Lectka, T. Reactive Ketenes Through a Carbonate/Amine Shuttle Deprotonation Strategy: Catalytic, Enantioselective α-Bromination of Acid Chlorides. Org. Lett. 2001, 3, 2049-2051.
58. (b) Taggi, A. E.; Wack, H.; Hafez, A. M.; France, S.; Lectka, T. The Generation of Ketenes from Acid Chlorides Using NaH/Crown Ether Shuttle-Deprotonation for use in Asymmetric Catalysis. Org. Lett. 2002, 4, 627-629.
59. 2. See ref 30.
60. Dudding, T.; Hafez, A. M.; Taggi, A. E.; Wagerle, T. R.; Lectka, T. A Catalyst that Plays Multiple Roles: Asymmetric Synthesis of β-Substituted Aspartic Acid Derivatives Through a Four-Stage, One-Pot Procedure. Org. Lett. 2002, 4, 387-390.
61. France, S.; Wack, H.; Hafez, A. M.; Taggi, A. E.; Witsil, D. R.; Lectka, T. Bifunctional Asymmetric Catalysis: A Tandem Nucleophile/Lewis Acid Promoted Synthesis of β-Lactams. Org. Lett. 2002, 4, 1603-1605.
62. Aggarwal, V. K.; Dean, D. K.; Mereu, A.; Williams, R. Rate Acceleration of the Baylis-Hillman Reaction in Polar Solvents (Water and Formamide). Dominant Role of Hydrogen Bonding, Not Hydrophobic Effects, Is Implicated. J. Org. Chem. 2002, 67, 510-514.
63. We have obtained IR evidence that supports metal chelation to the zwitterionic enolate.
64. Wack, H.; Taggi, A. E.; Hafez, A. M.; Drury, W. J., III.; Lectka, T. Catalytic, Asymmetric α-Halogenation. J. Am. Chem. Soc. 2001, 123, 1531-1532.
65. (a) Hafez, A. M.; Taggi, A. E.; Wack, H.; Drury, W. J., III.; Lectka, T. Column Asymmetric Catalysis for β-Lactam Synthesis. Org. Lett. 2000, 2, 3963-3965.
66. Hafez, A. M.; Taggi, A. E.; Dudding, T.; Lectka, T. Asymmetric Catalysis on Sequentially-Linked Columns. J. Am. Chem. Soc. 2001, 123, 10853-10859.