Synthesis of the novel chiral catalysts by click chemistry and their application

Synthetic Communications

Volumn 38, Issue 9, 2008, Pages 1470-1477

  Li, Qian ^a   Li, Le ^a   Pei, Wenbo ^a   Wang, Shanwei ^a   Zhang, Zhengpu ^a  

^a NANKAI UNIVERSITY   (China)

Author keywords

Asymmetric alkylations; Cinchona alkoloids; Click reaction; Phase transfer catalysis

Indexed keywords

CINCHONINE; GLYCINE DERIVATIVE; N DIPHENYLMETHYLENEGLYCINE TERT BUTYL ESTER; SODIUM CHLORIDE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; BENZYLATION; CATALYST; CHEMICAL STRUCTURE; CYCLOADDITION; SYNTHESIS;

EID: 42149127092     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910801914020     Document Type: Article

References (33)

1. O'Donnell, M. J.; Bennett, W. D.; Wu, S. The stereoselective synthesis of α-amino acids by phase-transfer catalysis. J. Am. Chem. Soc. 1989, 111, 2353-2355.
2. Lygo, B.; Wainwright, P. G. A new class of asymmetric phase-transfer catalysts derived from Cinchona alkaloids-application in the enantioselective synthesis of α-amino acids. Tetrahedron Lett. 1997, 38, 8595-8598.
3. Corey, E. J.; Xu, F.; Noe, M. C. A rational approach to catalytic enantioselective enolate alkylation using a structurally rigidified and defined chiral quaternary ammonium salt under phase transfer conditions. J. Am. Chem. Soc. 1997, 119, 12414-12415.
4. (a) Lipkowitz, K. B.; Cavanaugh, M. W.; Baker, B.; O'Donnell, M. J. Theoretical studies in molecular recognition: asymmetric induction of benzophenone imine ester enolates by the benzylcinchoninium ion. J. Org. Chem. 1991, 56, 5181-5192;
5. (b) O'Donnell, M. J.; Wu, S.; Huffman, J. C. A new active catalyst species for enantioselective alkylation by phase-transfer catalysis. Tetrahedron 1994, 50, 4507-4518;
6. (c) Lygo, B.; Crosby, J.; Lowdon, T. R.; Wainwright, P. G. (c) Structure-selectivity studies on catalysts for the phase-transfer catalysed asymmetric alkylation of glycine imine esters. Tetrahedron 2001, 57, 2391-2402;
7. (d) Lygo, B.; Crosby, J. A.; Wainwright, P. G. Studies on the enantioselective synthesis of α-amino acids via asymmetric phase-transfer catalysis. Tetrahedron 2001, 57, 2403-2409.
8. (a) Jew, S.-S.; Jeong, B.-S.; Yoo, M.-S.; Park, Y.; Park, H.-G. An unusual electronic effect of an aromatic-F in phase-transfer catalysts derived from Cinchona-alkaloid. Org. Lett. 2002, 4, 4245-4248;
9. (b) Park, H.-G.; Jeong, B.-S.; Yoo, M.-S.; Lee, J.-H.; Park, B.-S.; Kim, M. G.; Jew, S.-S. Highly efficient orthofluoro-dimeric cinchona-derived phase-transfer catalysts. Tetrahedron Lett. 2003, 44, 3497-3500;
10. (c) Yoo, M.-S; Jeong, B.-S.; Lee, J.-H.; Jew, S.-S. Evidence of the electronic factor for the highly enantioselective catalytic efficiency of Cinchona-derived phase-transfer catalysts. Org. Lett. 2005, 7, 1129-1131.
11. (a) Jew, S.-S.; Jeong, B.-S.; Yoo, M.-S.; Huh, H.; Park, H.-G. Synthesis and application of dimeric Cinchona alkaloid phase-transfer catalysts: α,α′-bis [O(9)-allylcinchonidinium]-o, m, or p-xylene dibromide. Chem. Commun. 2001, 1244-1245;
12. (b) Park, H.-G.; Jeong, B.-S.; Yoo, M.-S.; Lee, J.-H.; Park, M.-K.; Lee, Y.-J.; Kim, M.-J.; Jew, S.-S. Highly enantioselective and practical cinchona-derived phase-transfer catalysts for the synthesis of α-amino acids. Angew. Chem. Int. Ed. 2002, 41, 3036-3038;
13. (c) Chinchilla, R.; Mazon, P.; Najera, C. New dimeric anthracenyl-derived cinchona quaternary ammonium salts as phase-transfer catalysts for the asymmetric synthesis of α-amino acids. Tetrahedron: Asymmetry 2002, 13, 927-931;
14. (d) Siva, A.; Murugan, E. Syntheses of new dimeric-cinchona alkaloid as a chiral phase transfer catalysts for the alkylation of schiff base. J. Mol. Catal. A: Chem. 2005, 241, 111-117;
15. (e) Li, L.; Zhang, Z. P.; Zhu, X. X.; Popa, A.; Wang, S. W. Asymmetric alkylation of a tert-butyl benzophenone schiff base derivative in water. Synlett 2005, 12, 1873-1876.
16. (a) Park, H.-G.; Jeong, B.-S.; Yoo, M.-S.; Park, M.-K.; Huh, H.; Jew, S.-S. Trimeric cinchona alkaloid phase-transfer catalyst: α, α′,α″-tris[o(9)-allylcinchonidinium] mesitylene tribromide. Tetrahedron Lett. 2002, 42, 4645-4648;
17. (b) Siva, A.; Murugan, E. A new trimeric cinchona alkaloid as a chiral phase-transfer catalyst for the synthesis of asymmetric α-amino acids. Synthesis 2005, 17, 2927-2933.
18. Guillena, G.; Kreiter, R.; van de Coevering, R.; Gebbink, R. J. M. K.; van Koten, G.; Mazón, P.; Chinchilla, R.; Nájera, C. Chiroptical properties and applications in PTC of new dendritic cinchonidine-derived ammonium salts. Tetrahedron: Asymmetry 2003, 14, 3705-3712.
19. 2-symmetric chiral phase-transfer catalyst for practical asymmetric synthesis of α-amino acids. J. Am. Chem. Soc. 1999, 121, 6519-6520;
20. (b) Ooi, T.; Uematsu, Y.; Kameda, M.; Maruoka, K. Conformationally flexible, chiral quaternary ammonium bromides for asymmetric phase-transfer catalysis. Angew. Chem., Int. Ed. 2002, 41, 1551-1554;
21. (c) Ooi, T.; Tayama, E.; Maruoka, K. Highly stereo-selective n-terminal functionalization of small peptides by chiral phase-transfer catalysis. Angew. Chem. Int. Ed. 2003, 42, 579-582;
22. 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;
23. (e) Kitamura, M.; Shirakawa, S.; Maruoka, K. Powerful chiral phase-transfer catalysts for the asymmetric synthesis of α-alkyl- and α,αdialkyl-α-amino acids. Angew. Chem. Int. Ed. 2005, 44, 1549-1551.
24. (a) Tornfe, C. W.; Meldal, M. In Peptidotriazoles: Copper(I)-Catalyzed 1,3-Dipolar Cycloadditions on Solid Phase; Lebl, M., Houghten, R. A., Eds.; American Peptide Society and Kluwer Academic Publishers: San Diego, 2001, p. 263;
25. (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;
26. (c) 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.
27. (a) Kolb, H. C.; Sharpless, K. B. The growing impact of click chemistry on drug discovery. Drug Discov. Today 2003, 8, 1128;
28. I-catalyzed alkyne-azide "click" cycloadditions from a mechanistic and synthetic perspective. Eur. J. Org. Chem. 2006, 51-68.
29. Kacprzak, K. M.; Maier, N. M.; Lindner, W. Highly efficient immobilization of cinchona alkaloid derivatives to silica gel via click chemistry. Tetrahedron Lett. 2006, 47, 8721-8726.
30. (a) Huisgen, R. 1,3-dipolar cycloadditions. Past and future. Angew. Chem. Int. Ed. Engl. 1963, 2, 565-598;
31. (b) Huisgen, R. Kinetics and mechanism of 1,3-dipolar cycloadditions. Angew. Chem. Int. Ed. Engl. 1963, 2, 633-645;
32. (c) 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.
33. Lutz, J.-F. 1,3-Dipolar cycloadditions of azides and alkynes: a universal ligation tool in polymer and materials science. Angew. Chem. Int. Ed. 2007, 46, 1018-1025.