Asymmetric organic catalysis with modified cinchona alkaloids

Accounts of Chemical Research

Volumn 37, Issue 8, 2004, Pages 621-631

  Tian, Shi Kai ^a   Chen, Yonggang ^a,b   Hang, Jianfeng ^a   Tang, Liang ^a   McDaid, Paul ^a   Deng, Li ^a  

^a BRANDEIS UNIVERSITY   (United States)

^b AMERICAN HEART ASSOCIATION   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACID ANHYDRIDE; CINCHONA ALKALOID; KETONE; ORGANIC COMPOUND; THIOL DERIVATIVE;

ADDITION REACTION; ARTICLE; CATALYSIS; CHEMICAL REACTION KINETICS; CHIRALITY; CYANATION; DIHYDROXYLATION; ENANTIOSELECTIVITY; SYNTHESIS;

EID: 4143136647     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar030048s     Document Type: Article

References (47)

1. Comprehensive Asymmetric Catalysis, Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: New York, 1999; Vols. I-III.
2. (a) Ruble, J. C.; Fu, G. C. Chiral π-Complexes of Heterocycles with Transition Metals: A Versatile New Family of Nucleophilic Catalysts. J. Org. Chem. 1996, 61, 7230-7231.
3. (b) For a review, see: Fu, G. C. Enantioselective Nucleophilic Catalysis with "Planar-Chiral" Heterocycles. Acc. Chem. Res. 2000, 33, 412-420 and references therein.
4. Oriyama, T.; Imai, K.; Hosoya, T.; Sano, T. Asymmetric Acylation of meso-Diols with Benzoyl Halide in the Presence of a Chiral Diamine. Tetrahedron Lett. 1998, 39, 397-400.
5. (a) Denmark, S. E.; Stavenger, R. A.; Su, X. P.; Wong, K. T.; Nishigaichi, Y. Asymmetric Catalysis with Chiral Lewis Bases. Pure Appl. Chem. 1998, 70, 1469-1476.
6. (b) For a review, see: Denmark, S. E.; Stavenger, R. A. Asymmetric Catalysis of Aldol Reactions with Chiral Lewis Bases. Acc. Chem. Res. 2000, 33, 432-440.
7. For a comprehensive review of a wide range of asymmetric catalysis of cinchona alkaloids, see: Kacprzak, K.; Gawronski, J. Cinchona Alkaloids and Their Derivatives: Versatile Catalysts and Ligands in Asymmetric Synthesis. Synthesis 2001, 961-998.
8. Pracejus, H. Asymmetrische Synthesen mit Ketene. I Justus Liebigs Ann. Chem. 1960, 634, 9-22.
9. Wynberg, H. Asymmetric Catalysis by Alkaloids. Top. Stereochem. 1986, 16, 87-129.
10. Wynberg, H.; Staring, E. G. J. Asymmetric Synthesis of (S)- and (R)-Malic Acid from Ketene and Chloral. J. Am. Chem. Soc. 1982, 104, 166-168.
11. Kagan, H. B. Historical Perspective. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin, 1999; Chapter 2.
12. For a review, see: Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Catalytic Asymmetric Dihydroxylation. Chem. Rev. 1994, 94, 2483-2547.
13. Marko, I. E.; Svendsen, J. S. Dihydroxylation of Carbon-Carbon Double Bonds. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: New York, 1999; Vols. I-III, Chapter 20.
14. Corey, E. J.; Noe, M. C. Rigid and Highly Enantioselective Catalyst for the Dihydroxytation of Olefins Using Osmium Tetraoxide Clarifies the Origin of Enantiospecificity. J. Am. Chem. Soc. 1993, 775, 12579-12580.
15. For a review, see: Chen, Y.; McDaid, P.; Deng, L. Asymmetric Alcoholysis of Cyclic Anhydrides. Chem. Rev. 2003, 103, 2965-2984.
16. (a) Hiratake, J.; Yamamoto, Y.; Oda, J. Catalytic Asymmetric Induction from Prochiral Cyclic Acid Anhydrides Using Cinchona Alkaloids. J. Chem. Soc., Chem. Commun. 1985, 1717-1719.
17. (b) Hiratake, J.; Inagaki, M.; Yamamoto, Y.; Oda, J. Enantiotopic-Group Differentiation-Catalytic Asymmetric Ring-Opening of Prochiral Cyclic Acid Anhydrides with Methanol, Using Cinchona Alkaloids. J. Chem. Soc., Perkin. Trans. 1 1987, 1053-1058.
18. Aitken, R. A.; Gopat, J.; Hirst, J. A. Catalytic Asymmetric Synthesis of Highly Functionalized Compounds with 6 Contiguous Stereocenters. J. Chem. Soc., Chem. Commun. 1988, 632-634.
19. (a) Bolm, C.; Gerlach, A.; Dinter, C. L. Simple and Highly Enantioselective NonenzymaticRing Opening of Cyclic Prochiral Anhydrides. Synlett 1999, 195-196.
20. (b) Bolm, C.; Schiffers I.; Dinter, C. L.; Gerlach, A. Practical and Highly Enantioselective Ring Opening of Cyclic maso-anhydrides Mediated by Cinchona Alkaloids. J. Org. Chem. 2000, 65, 6984-6991.
21. Chen, Y.; Tian, S.-K.; Deng, L. A Highly Enantioselective Catalytic Desymmetrization of Cyclic Anhydrides with Modified Cinchona Alkaloids. J. Am. Chem. Soc. 2000, 122, 9542-9543.
22. Choi, C.; Tian, S.-K.; Deng, L. A Formal Catalytic Asymmetric Synthesis of (+)-Biotin with Modified Cinchona Alkaloids. Synthesis 2001, 1737-1741.
23. For a review, see: Eames, J. Parallel Kinetic Resolutions. Angew. Chem., Int. Ed. 2000, 39, 885-888.
24. Chen, Y.; Deng, L. Parallel Kinetic Resolutions of Monosubstituted Succinic Anhydrides Catalyzed by a Modified Cinchona Alkaloid. J. Am. Chem. Soc. 2001, 123, 11302-11303.
25. For preparations of UNCAs from α-amino acids, see: Fuller, W. D.; Goodman, M.; Naider, F. R.; Zhu, Y. F. Urethane-Protected α-Amino Acid N-Carboxyanhydrides and Peptide Synthesis. Biopolymers (Peptide Sci.) 1996, 40, 183-205.
26. Hang, J.; Tian, S.-K.; Tang, L.; Deng, L. Asymmetric Synthesis of α-Amino Acids via Cinchona Alkaloid-Catalyzed Kinetic Resolution of Urethane-Protected α-Amino Acid N-Carboxyanhydrides. J. Am. Chem. Soc. 2001, 123, 12696-12697.
27. Toyooka, K.; Takeuchi, Y.; Kubota, S. A Novel and Facile Synthesis of 5-Substituted 1,3-Dioxolane-2,4-Diones using Trichloromethyl Chloroformate. Heterocycles 1989, 29, 975-978.
28. Tang, L.; Deng, L. Dynamic Kinetic Resolution via Dual-function Catalysis of Modified Cinchona Alkaloids: Asymmetric Synthesis of α-Hydroxy Carboxylic Acids. J. Am. Chem. Soc. 2002, 124, 2870-2871.
29. (a) France, S.; Guerin, D. J.; Miller, S. J.; Lectka, T. L. Nucleophilic Chiral Amines as Catalysts in Asymmetric Synthesis. Chem. Rev. 2003, 103, 2985-3012.
30. (b) Dalko, P. I.; Moisan, L. Enantioselective Organocatalysis. Angew. Chem., Int. Ed. 2001, 40, 3726-3748 and references therein.
31. (a) Kitamura, M.; Tokunaga, M.; Noyori, R. Quantitative Expression of Dynamic Kinetic Resolution of Chirally Labile Enantiomers: Stereoselective Hydrogenation of 2-Substituted 3-Oxo Carboxylic Esters Catalyzed by BINAP-Ruthenium(II) Complexes. J. Am. Chem. Soc. 1993, 115, 144-152.
32. (b) For a review see: Ward, R. S. Dynamic Kinetic Resolution. Tetrahedron: Asymmetry 1995, 6, 1475-1490 and references therein.
33. Hang, J.; Li, H.; Deng, L. Development of a Rapid, Room-Temperature Dynamic Kinetic Resolution for Efficient Asymmetric Synthesis of α-Aryl Amino Acids. Org. Lett. 2002, 4, 3321-3324.
34. For a review, see: Corey, E. J.; Guzman-Perez, A. The Catalytic Enantioselective Construction of Molecules with Quaternary Carbon Stereocenters. Angew. Chem., Int. Ed. Engl. 1998, 37, 388-401.
35. Poirier, D.; Berthiaume, D.; Boivin, R. P. Unexpected Formation of O-Methoxycarbonyl Cyanohydrin Showing Potential as a Protective Group of Ketones. Synlett 1999, 1423-1425.
36. Tian, S.-K.; Deng, L. A Highly Enantioseletive Chiral Lewis Base-Catalyzed Asymmetric Cyanation of Ketones. J. Am. Chem. Soc. 2001, 723, 6195-6196.
37. In parallel with our studies with chiral Lewis bases, highly enantiosetective cyanation of ketones with chiral Lewis acids were also reported: (a) Hamashima, Y.; Kanai, M.; Shibasaki, M. Catalytic Enantioselective Cyanosilylation of Ketones. J. Am. Chem. Soc. 2000, 122, 7412-7413.
38. (b) Deng, H.; Isler, M. P.; Snapper, M. L.; Hoveyda, A. H. Aluminum-Catalyzed Asymmetric Addition of TMSCN to Aromatic and Aliphatic Ketones Promoted by an Easily Accessible and Recyclable Peptide Ligands. Angew. Chem, Int. Ed. 2002, 41, 1009-1012.
39. Hiemstra, H.; Wynberg, H. Addition of Aromatic Thiols to Conjugated Cycloalkenones Catalyzed by Chiral β-Hydroxy Amines. A Mechanistic Study on Homogeneous Catalytic Asymmetric Synthesis. J. Am. Chem. Soc. 1981, 103, 417-430.
40. McDaid, P.; Chen, Y.; Deng, L. A Highly Enantioselective and General Conjugate Addition of Thiols to Cyclic Enones with an Organic Catalyst. Angew. Chem., Int. Ed. 2002, 41, 338-340.
41. Suzuki, K.; Ikegawa, A.; Mukaiyama, T. The Enantioselective Michael Addition of Thiols to Cycloalkenones by Using (2S,4S)-2-Anilinomethyl-1-ethyl-4- hydroxypyrrolidine as Chiral Catalyst. Bull. Chem. Soc. Jpn. 1982, 55, 3277-3282.
42. Calter, M. A. Catalytic, Asymmetric Dimerization of Methylketene. J. Org. Chem, 1996, 61, 8006-8007.
43. Iwalbuchi, Y.; Nakatani, M.; Yokoyama, N.; Hatekeyama, S. J. Chiral Amine-Catalyzed Asymmetric Baylis-Hillman Reaction: A Reliable Route to Highly Enantiomerically Enriched (α-Methylene-β-hydroxylesters. J. Am. Chem. Soc. 1999, 121, 10219-10220.
44. (a) Taggi, A. E.; Hafez, A. M.; Wack, H.; Young, B.; Drury, W. J.; Lectka, T. Catalytic Asymmetric Synthesis of β-Lactams. J. Am. Chem. Soc. 2000, 122, 7831-7832.
45. (b) Wack, H.; Taggi, A. E.; Hafez, A. M.; Drury, W. J.; Lectka, T. Catalytic, Asymmetric α-Halogenation. J. Am. Chem. Soc. 2001, 123, 1531-1532.
46. (a) Cortez, G. S.; Tennyson, R. L.; Romo, D. Intramolecular, Nucleophile-Catalyzed Aldol-Lactonization (NCAL) Reactions: Catalytic, Asymmetric Synthesis of Bicyclic β-Lactones. J. Am. Chem. Soc. 2001, 123, 7945-7946.
47. (b) Cortez, G. S.; Oh, S. H.; Romo, D. Bicyclic β-Lactones via Intramolecular NCAL Reactions with Cinchona Alkaloids: Effect of the C9-Susbstituent on Enantioselectivity and Catalyst Conformation. Synthesis 2001, 1731-1736.