Applications of planar-chiral heterocycles as ligands in asymmetric catalysis

Accounts of Chemical Research

Volumn 39, Issue 11, 2006, Pages 853-860

  Fu, Gregory C ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HETEROCYCLIC COMPOUND; LIGAND;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; CYCLIZATION; HETEROCYCLIC COMPOUNDS; LIGANDS; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 33845488531     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar068115g     Document Type: Article

References (70)

1. For leading references, see (a) Chiral Intermediates and Chiral Drugs; Challener, C. A., Ed.; Ashgate: Brookfield, VT, 2001.
2. (b) The Impact of Stereochemistry on Drug Development and Use; Aboul-Enein, H. Y., Ed.; Wiley: New York, 1997.
3. (c) Chirality in Drug Design and Synthesis; Brown, C., Ed.; Academic: New York, 1990.
4. (d) For the Policy Statement of the Food and Drug Administration on the development of new stereoisomeric drugs, see http://www.fda.gov/cder/guidance/ stereo.htm.
5. See also Blumenstein, J. J. Chiral drugs: Regulatory aspects. In Chirality in Industry II; Collins, A. N., Sheldrake, G. N., Crosby, J., Eds.; Wiley: New York, 1997.
6. Rouhi, A. M. Chiral chemistry. Chem. Eng. News 2004, June 14, 51.
7. For leading references, see (a) Methods of Organic Chemistry (Houben-Weyl): Stereoselective Synthesis; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; George Thieme Verlag: New York, 1995.
8. (b) Chirality in Industry, Collins, A. N., Sheldrake, G. N., Crosby, J., Eds.; Wiley: New York, 1992.
9. (c) Chirality in Industry II; Collins, A. N., Sheldrake, G. N., Crosby, J., Eds.; Wiley: New York, 1997.
10. For leading references, see (a) Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: New York, 1999; Vol. 1-3.
11. (b) Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 2000.
12. (c) Asymmetric Catalysis on Industrial Scale; Blaser, H. U., Schmidt, E., Eds.; Wiley-VCH: New York, 2004.
13. For some leading references, see Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Comprehensive Asymmetric Catalysis; Springer: New York, 1999.
14. Cahn, R. S.; Ingold, C.; Prelog, V. Specification of molecular chirality. Angew. Chem., Int. Ed. Engl. 1966, 5, 385-415.
15. See also Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds; Wiley-Interscience: New York, 1994.
16. For some early examples, see Togni, A. Planar-chiral ferrocenes: Synthetic methods and applications. Angew. Chem., Int. Ed. Engl. 1996, 35, 1475-1477. Most of these ligands also possess central chirality.
17. Simultaneously with and independent of our initial contribution (Qiao, S.; Fu, G. C. The first application of a planar-chiral phosphorus heterocycle in asymmetric catalysis: Enantioselective hydrogenation of dehydroamino acids. J. Org. Chem. 1998, 63, 4168-4169),
18. Ganter described the use of a planar-chiral heterocycle as a ligand in asymmetric catalysis (Ganter, C.; Glinsboeckel, C.; Ganter, B. New P,N-chelate ligands based on pyridyl-substituted phosphaferrocenes. Eur. J. Inorg. Chem. 1998, 1163-1168).
19. For leading references, see Fu, G. C. Asymmetric catalysis with "planar-chiral" derivatives of DMAP. Acc. Chem. Res. 2004, 37, 542-547.
20. (a) For examples and leading references, see Sadimenko, A. P. Organometallic compounds of pyrrole, indole, carbazole, phospholes, siloles, and boroles. Adv. Heterocycl. Chem. 2001, 79, 1-197.
21. (b) For pioneering studies, see Carmichael, D.; Mathey, F. New trends in phosphametallocene chemistry. Top. Curr. Chem. 2002, 220, 27-51.
22. Togni, A., Hayashi, T., Eds.; Ferrocenes; VCH: New York, 1995.
23. Dyker, G.; Heiermann, J.; Miura, M.; Inoh, J.-I.; Pivsa-Art, S.; Satoh, T.; Nomura, M. Palladium-catalyzed arylation of cyclopentadienes. Chem. - Eur. J. 2000, 6, 3426-3433.
24. 2-symmetric bisazaferrocene and its application in the enantioselective Cu(I)-catalyzed cyclopropanation of olefins. J. Am. Chem. Soc. 1998, 120, 10270-10271.
25. For some leading references, see Lebel, H.; Marcoux, J.-F.; Molinaro, C.; Charette, A. B. Stereoselective cyclopropanation reactions. Chem. Rev. 2003, 103, 977-1050.
26. Doyle, M. P.; Hu, W.; Chapman, B.; Marnett, A. B.; Peterson, C. S.; Vitale, J. P.; Stanley, S. A. Enantiocontrolled macrocycle formation by catalytic intramolecular cyclopropanation. J. Am. Chem. Soc. 2000, 122, 5718-5728.
27. 2-symmetric, planar-chiral bipyridine ligand. Application to the catalytic enantioselective cyclopropanation of olefins. Chem. Commun. 2000, 377-378.
28. For leading references, see Davies, H. M. L. C-H insertion reactions, cycloadditions, and ylide formation of diazo compounds. In Comprehensive Asymmetric Catalysis (Supplement 1); Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: New York, 2004, pp 83-94.
29. Bulugahapitiya, P.; Landais, Y.; Parra-Rapado, L.; Planchenault, D.; Weber, V. A stereospecific access to allylic systems using rhodium(II)-vinyl carbenoid insertion into Si-H, O-H, and N-H bonds. J. Org. Chem. 1997, 62, 1630-1641.
30. For leading references to metal-catalyzed insertions of diazo compounds into O-H bonds, see Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; Wiley: New York, 1998; Chapters 8.3 and 8.4.
31. Maier, T. C.; Fu, G. C. Catalytic enantioselective O-H insertion reactions. J. Am. Chem. Soc. 2006, 128, 4594-4595.
32. For leading references to the synthesis and the utility of α-hydroxycarbonyl compounds, see Chen, B.-C.; Zhou, P.; Davis, F. A.; Ciganek, E. α-Hydroxylation of enolates and silyl enol ethers. Org. React. 2003, 62, 1-356.
33. Akutagawa, S. Industrial applications: Asymmetric isomerization of olefins. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: New York, 1999; Chapter 41.4.
34. Tani, K. Asymmetric isomerization of allylic compounds and the mechanism. Pure Appl. Chem. 1985, 57, 1845-1854.
35. (a) Tanaka, K.; Qiao, S.; Tobisu, M.; Lo, M. M.-C.; Fu, G. C. Enantioselective isomerization of allylic alcohols catalyzed by a rhodium/phosphaferrocene complex. J. Am. Chem. Soc. 2000, 122, 9870-9871.
36. (b) Tanaka, K.; Fu, G. C. A versatile new catalyst for the enantioselective isomerization of allylic alcohols to aldehydes: Scope and mechanistic studies. J. Org. Chem. 2001, 66, 8177-8186.
37. Inoue, S.-I.; Takaya, H.; Tani, K.; Otsuka, S.; Sato, T.; Noyori, R. Mechanism of the asymmetric isomerization of allylamines to enamines catalyzed by 2,2′-bis(diphenylphosphino)-1,1′binaphthyl-rhodium complexes. J. Am. Chem. Soc. 1990, 112, 4897-4905.
38. Nishiyama, H. Asymmetric hydrosilylation and related reactions. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: New York, 1999; Chapter 6.3.
39. 5 ligand to achieve high enantioselectivity. J. Am. Chem. Soc. 2001, 123, 353-354.
40. For leading references, see (a) The β-Lactamases: A Major Cause of Resistance of β-Lactam Antibiotics and β-Lactamase Inhibitors; Mascaretti, O. A., Ed.; Bentham: Hilversum, The Netherlands, 1999.
41. (b) Chemistry and Biology of β-Lactam Antibiotics; Morin, R. B., Gorman, M., Eds.; Academic: New York, 1982; Vol. 1-3.
42. (a) Synthesis of β-Lactam Antibiotics; Bruggink, A., Ed.; Kluwer: Dordrecht, The Netherlands, 2001.
43. (b) The Chemistry of β-Lactams; Page, M. I., Ed.; Chapman and Hall: London, U.K., 1997.
44. (c) Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon: New York, 1996; Vol. 1B, Chapters 1.18-1.20.
45. (d) The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH: New York, 1993.
46. For leading references, see France, S.; Weatherwax, A.; Taggi, A. E.; Lectka, T. Advances in the catalytic, asymmetric synthesis of β-lactams. Acc. Chem. Res. 2004, 37, 592-600.
47. Kinugasa, M.; Hashimoto, S. Reactions of copper(I) phenylacetylide with nitrones. J. Chem. Soc., Chem. Commun. 1972, 466-467.
48. Miura, M.; Enna, M.; Okuro, K.; Nomura, M. Copper-catalyzed reaction of terminal alkynes with nitrones. Selective synthesis of 1-aza-1-buten-3-yne and 2-azetidinone derivatives. J. Org. Chem. 1995, 60, 4999-5004.
49. Lo, M. M.-C.; Fu, G. C. Cu(I)/bis(azaferrocene)-catalyzed enantioselective synthesis of β-lactams via couplings of alkynes with nitrones. J. Am. Chem. Soc. 2002, 124, 4572-4573.
50. The 4-anisyl substituent is a common nitrogen protecting group for β-lactams. (a) Wild, H. Protective groups in β-lactam chemistry. In The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH: New York, 1993; Chapter 1.
51. (b) Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 3rd ed.; Wiley: New York, 1999; pp 636-637.
52. (a) Shintani, R.; Lo, M. M.-C.; Fu, G. C. Synthesis and application of planar-chiral phosphaferrocene-oxazolines, a new class of P,N-ligands. Org. Lett. 2000, 2, 3695-3697.
53. (b) Shintani, R.; Fu, G. C. Copper-catalyzed enantioselective conjugate addition of diethylzinc to acyclic enones in the presence of planar-chiral phosphaferrocene-oxazoline ligands. Org. Lett. 2002, 4, 3699-3702.
54. Shintani, R.; Fu, G. C. Catalytic enantioselective synthesis of β-lactams: Intramolecular Kinugasa reactions and interception of an intermediate in the reaction cascade. Angew. Chem., Int. Ed. 2003, 42, 4082-4085.
55. For a review, see Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products; Padwa, A., Pearson, W. H., Eds.; Wiley: New York, 2003; Vol. 59.
56. For a review of catalytic asymmetric cycloadditions, see Maruoka, K. Asymmetric cycloaddition reactions. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: New York, 1999; pp 467-491.
57. (a) Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. A stepwise Huisgen cycloaddition process: Copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes. Angew. Chem., Int. Ed. 2002, 41, 2596-2599.
58. (b) Tornøe, C. W.; Christensen, C.; Meldal, M. Peptidotriazoles on solid phase: [1,2,3]-Triazoles by regiospecific copper(I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides. J. Org. Chem. 2002, 67, 3057-3064.
59. Dorn, H.; Otto, A. Syntheses by means of 1-alkylidene- and 1-(arylalkylidene)-3-pyrazolidinone N,N-betaines, a new type of stable azomethine imine. Angew. Chem., Int. Ed. Engl. 1968, 7, 214-215.
60. For example, see Panfil, I.; Urbanczyk-Lipkowska, Z.; Suwinska, K.; Solecka, J.; Chmielewski, M. Synthesis of pyrazolidinone analogs of β-lactam antibiotics. Tetrahedron 2002, 58, 1199-1212.
61. For example, see Ternansky, R. J.; Draheim, S. E. The synthesis and biological evaluation of pyrazolidinone antibacterial agents. In Recent Advances in the Chemistry of β-Lactam Antibiotics; Bentley, P. H., Southgate, R. H., Eds.; Royal Society of Chemistry: London, U.K., 1989; pp 139-156.
62. Shintani, R.; Fu, G. C. A new copper-catalyzed [3+2] cycloaddition: Enantioselective coupling of terminal alkynes with azomethine imines to generate five-membered nitrogen heterocycles. J. Am. Chem. Soc. 2003, 125, 10778-10779.
63. For a classic review of kinetic resolutions, see Kagan, H. B.; Fiaud, J. C. Kinetic resolution. Top. Stereochem. 1988, 18, 249-330.
64. For a review, see Cardona, F.; Goti, A.; Brandi, A. Kinetic resolutions by means of cycloaddition reactions. Eur. J. Org. Chem. 2001, 2999-3011.
65. Suarez, A.; Downey, C. W.; Fu, G. C. Kinetic resolutions of azomethine imines via copper-catalyzed [3+2] cycloadditions. J. Am. Chem. Soc. 2005, 127, 11244-11245.
66. For leading references to the chemistry of azomethine imines, see Schantl, J. G. Product class 19: Azomethine imines. Sci. Synth. 2004, 27, 731-824.
67. In addition to the processes that have been discussed in this Account, we have examined (a) hydrogenations: Qiao, S.; Fu, G. C. The first application of a planar-chiral phosphorus heterocycle in asymmetric catalysis: Enantioselective hydrogenation of dehydroamino acids. J. Org. Chem. 1998, 63, 4168-4169.
68. (b) allylic alkylations: Shintani, R.; Lo, M. M.-C.; Fu, G. C. Synthesis and application of planar-chiral phosphaferrocene-oxazolines, a new class of P,N-ligands. Org. Lett. 2000, 2, 3695-3697.
69. (c) ring expansions: Lo, M. M.-C.; Fu, G. C. Applications of planar-chiral heterocycles in enantioselective catalysis: Cu(I)/bisazaferrocene- catalyzed asymmetric ring expansion of oxetanes to tetrahydrofurans. Tetrahedron 2001, 57, 2621-2634.
70. (d) conjugate additions: Shintani, R.; Fu, G. C. Copper-catalyzed enantioselective conjugate addition of diethylzinc to acyclic enones in the presence of planar-chiral phosphaferrocene-oxazoline ligands. Org. Lett. 2002, 4, 3699-3702.