Enantioselective synthesis of β-amino esters bearing a quinazoline moiety via a Mannich-type reaction catalyzed by a cinchona alkaloid derivative

Science China Chemistry

Volumn 56, Issue 3, 2013, Pages 321-328

  He, Ming ^a   Pan, Zhao Xi ^a   Bai, Song ^a   Li, Pei ^a   Zhang, Yu Ping ^a   Jin, Lin Hong ^a   Hu, De Yu ^a   Yang, Song ^a   Song, Bao An ^a  

^a GUIZHOU UNIVERSITY   (China)

Author keywords

amino esters; Cinchona alkaloid based thiourea; enantioselective synthesis; Mannich reaction

Indexed keywords

1 ,3-DICARBONYL COMPOUNDS; AMINO ESTERS; CINCHONA ALKALOID; ENANTIOMERIC EXCESS; ENANTIOSELECTIVE SYNTHESIS; MANNICH REACTIONS; MANNICH-TYPE REACTIONS; QUINAZOLINES;

ALKALOIDS; CATALYSIS; ESTERIFICATION; ESTERS; METABOLITES; NITROGEN COMPOUNDS; SYNTHESIS (CHEMICAL);

ENANTIOSELECTIVITY;

EID: 84879692733     PISSN: 16747291     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11426-012-4822-4     Document Type: Conference Paper

References (82)

1. Davis FA, Szewczyk JM. Synthesis and applications of nonracemic β-amino aldehydes to the asymmetric synthesis of piperdines: (+)-dihydropinidine. Tetrahedron Lett, 1998, 39(33): 5951-5954
2. Seebach D, Kimmerlin T, Sebesta R, Campo MA, Beck AK. How we drifted into peptide chemistry and where we have arrived at. Tetrahedron, 2004, 60: 7455-7506
3. Shih C, Gossett LS, Gruber JM, Grossman CS, Andis SL, Schultz RM, Worzalla JF, Corbett TH, Metz JT. Synthesis and biological evaluation of novel cryptophycin analogs with modification in the beta-alanine region. Bioorg Med Chem Lett, 1999, 9(1): 69-74
4. Juaristi EED. Enantioselective Synthesis of β-Amino Acids. New York: Wiley-VCH, 1997
5. Mock WH, Chen H. Principles of hydroxamate inhibition of metalloproteases: Carboxypeptidase A. Biochemistry, 2000, 39(45): 13945-13952
6. Callahan JF, Huffman WF, Moore ML. Newlander KA. HIV protease inhibitors. US Patent, 5438118, 1995-08-01
7. Peukert S, Sun Y, Zhang R, Hurley B, Sabio M, Shen X, Gray C, Dzink-Fox J, Tao J, Cebula R, Wattanasin S. Design and structure-activity relationships of potent and selective inhibitors of undecaprenyl pyrophosphate synthase (UPPS): Tetramic, tetronic acids and dihydropyridin-2-ones. Bioorg Med Chem Lett, 2008, 18(6): 1840-1844
8. Carter PH, Cavallaro CL, Lucca GVD. Piperazinyl derivatives as modulators of chemokine receptor activity. US Patent, 20070179148, 2007-08-02
9. Crawford TD, Rawson DJ, Thorpe AJ. β-Amino acids derivatives. International application. WO2006120544, 2006-11-16
10. Tang W, Zhang X. Highly efficient synthesis of chiral beta-amino acid derivatives via asymmetric hydrogenation. Org Lett, 2002, 4(23): 4159-4161
11. Ma JA. Recent developments in the catalytic asymmetric synthesis of α- and β-amino acids. Angew Chem Int Ed, 2003, 42(36): 4290-4299
12. Sibi MP, Prabagaran N, Ghorpade SG, Jasperse CP. Enantioselective synthesis of α, β-disubstituted-β-amino acids. J Am Chem Soc, 2003, 125(39): 11796-11797
13. Edmonds MK, Graichen FH, Gardiner MJ, Abell AD. Enantioselective synthesis of alpha-fluorinated beta2-amino acids. Org Lett, 2008, 10(5): 885-887
14. Agami C, Cheramy S, Dechoux L, Melaimi M. Enantioselective synthesis of α, b-substituted β-amino acids. Tetrahedron, 2001, 57(1): 195-200
15. Vesely J, Rios R, Ibrahem I, Córdova A. Highly enantioselective organocatalytic addition of unmodified aldehydes to N-Boc protected imines: One-pot asymmetric synthesis of β-amino acids. Tetrahedron Lett, 2007, 48: 421-425
16. Liu TY, Long J, Li BJ, Jiang L, Li R, Wu Y, Ding LS, Chen YC. Enantioselective construction of quaternary carbon centre catalysed by bifunctional organocatalyst. Org Biomol Chem, 2006, 4(11): 2097-2099
17. Liu TY, Li R, Chai Q, Long J, Li BJ, Wu Y, Ding LS, Chen YC. Enantioselective Michael addition of α-substituted cyanoacetates to vinyl ketones catalyzed by bifunctional organocatalysts. Chem Eur J, 2007, 13(1): 319-327
18. Periasamy M, Suresh S, Ganesan SS. Addition of titanium ester enolates to aldimines containing a chiral α-methylbenzylamine moiety: Synthesis of chiral syn-β-amino esters. Tetrahedron: Asymmetr, 2006, 17(9): 1323-1331
19. Dziedzic P, Córdova A. Acyclic β-amino acid catalyzed asymmetric anti-selective Mannich-type reactions. Tetrahedron: Asymmetr, 2007, 18(9): 1033-1037
20. Kim SG, Park TH. An efficient synthesis of (+)-epi-cytoxazone via asymmetric organocatalysis. Tetrahedron: Asymmetr, 2008, 19(13): 1626-1629
21. Zhang ZW, Lu G, Chen MM, Lin N, Li YB, Hayashi T, Chan ASC. Organocatalytic asymmetric Mannich-type reaction of N-sulfonylimines with isocyanoacetate leading to optically active 2-imidazoline-4-carboxylates. Tetrahedron: Asymmetr, 2010, 21(13): 1715-1721
22. Jia YM, Mao ZF, Wang R. Asymmetric triple cascade organocatalytic reaction in water: construction of polyfunctional cyclohexene building blocks having multiple stereocenters. Tetrahedron: Asymmetr, 2011, 22(23): 2018-2023
23. Ting A, Schaus SE. Organocatalytic asymmetric Mannich reactions: New methodology, catalyst design, and synthetic applications. Eur J Org Chem, 2007(35): 5797-5815
24. Alcaide B, Almendros P. Organocatalytic reactions with acetaldehyde. Angew Chem Int Ed, 2008, 47(25): 4632-4634
25. Verkade JMM, van Hemert LJC, Quaedflieg PJLM, Rutjes FPJT. Organocatalysed asymmetric Mannich reactions. Chem Soc Rev, 2008, 37: 29-41
26. Wenzel AG, Jacobsen EN. Asymmetric catalytic Mannich reactions catalyzed by urea derivatives: Enantioselective synthesis of β-aryl-β-amino acids. J Am Chem Soc, 2002, 124(44): 12964-12965
27. Josephsohn NS, Snapper ML, Hoveyda AH. Ag-Catalyzed asymmetric Mannich reactions of enol ethers with aryl, alkyl, alkenyl and alkynyl imines. J Am Chem Soc, 2004, 126(12): 3734-3735
28. Lou S, Taoka BM, Jing A, Schaus SE. Asymmetric mannich reactions of beta-keto esters with acyl imines catalyzed by cinchona alkaloids. J Am Chem Soc, 2005, 127(32): 11256-11257
29. Cutting GA, Stainforth NE, John MP, Kociok-Köhn G, Willis MC. Direct catalytic enantioselective Mannich reactions: Synthesis of protected anti-α, β-diamino acids. J Am Chem Soc, 2007, 129(35): 10632-10633
30. Zhang HL, Mitsumori S, Utsumi N, Imai M, Garcia-Delgado N, Mifsud M, Albertshofer K, Cheong PH Y, Houk KN, Tanaka F, Barbas CFIII. Catalysis of 3-pyrrolidinecarboxylic acid and related pyrrolidine derivatives in enantioselective anti-Mannich-type reactions: Importance of the 3-acid group on pyrrolidine for stereocontrol. J Am Chem Soc, 2008, 130(3): 875-886
31. Kim DY, Kang YK. Organocatalytic highly enantio- and diastereoselective Mannich reaction of -ketoesters with N-Boc-aldimines. J Org Chem, 2009, 74(15): 5734-5737
32. Zhang H, Syed S, arbas CFIII. Highly enantio- and diastereoselective Mannich reactions of glycine schiff bases with in situ generated N-Boc-imines catalyzed by a cinchona alkaloid thiourea. Org Lett, 2010, 12(4): 708-711
33. Selected examples of metal-catalyzed Mannich-type reactions, see: (a) Cutting GA, Stainforth NE, John MP, Kociok-Kohn G, Willis MC. Direct catalytic enantioselective Mannich reactions: Synthesis of protected anti-α, β-diamino acids. J Am Chem Soc, 2007, 129(35): 10632-10633
34. Morimoto H, Lu G, Aoyama N, Matsunaga S, Shibasaki M. Lanthanum aryloxide/pybox-catalyzed direct asymmetric Mannich-type reactions using a trichloromethyl ketone as a propionate equivalent donor. J Am Chem Soc, 2007, 129(31): 9588-9589
35. Trost BM, Jaratjaroonphong J, Reutrakul V. A direct catalytic asymmetric Mannich-type reaction via a dinuclear zinc catalyst: Synthesis of either anti- or syn-α-hydroxy-β-amino ketones. J Am Chem Soc, 2006, 128(9): 2778-2779
36. Harada S, Handa S, Matsunaga S, Shibasaki M. Direct catalytic asymmetric Mannich-type reaction of N-(2-hydroxyacetyl)pyrrole promoted by an In(O-iPr)3/linked-BINOL complex: Use of an N-acylpyrrole as an ester equivalent donor. Angew Chem Int Ed, 2005, 44(28): 4365-4368
37. Okada A, Shibuguchi T, Ohshima T, Masu H, Yamaguchi K, Shibasaki M. Enantio- and diastereoselective catalytic Mannich-type reaction of a glycine Schiff base using a chiral two-center phase-transfer catalyst. Angew Chem Int Ed, 2005, 44(29): 4564-4567
38. For selected examples of direct organocatalytic Mannich-type reactions, see: (f) Yang JW, Chandler C, Stadler M, Kampen D, List B. Proline-catalysed Mannich reactions of acetaldehyde. Nature, 2008, 452(7186): 453-455
39. Zhang H, Mitsumori S, Utsumi N, Imai M, Garcia-Delgado N, Mifsud M, Albertshofer K, Cheong PHY, Houk KN, Tanaka F, Barbas CFIII. Catalysis of 3-pyrrolidinecarboxylic acid and related pyrrolidine derivatives in enantioselective anti-Mannich-type reactions: Importance of the 3-acid group on pyrrolidine for stereocontrol. J Am Chem Soc, 2008, 130(3): 875-886
40. Vesely J, Rios R, Ibrahem I, Córdova A. Highly enantioselective organocatalytic addition of unmodified aldehydes to N-Boc protected imines: One-pot asymmetric synthesis of β-amino acids. Tetrahedron Lett, 2007, 48: 421-425
41. Hashimoto T, Maruoka K. Design of axially chiral dicarboxylic acid for asymmetric Mannich reaction of arylaldehyde N-Boc imines and diazo compounds. J Am Chem Soc, 2007, 129(33): 10054-10055
42. Kano T, Yamaguchi Y, Tokuda O, Maruoka K. anti-Selective direct asymmetric Mannich reactions catalyzed by axially chiral amino sulfonamide as an organocatalyst. J Am Chem Soc, 2005, 127(47): 16408-16409
43. Enders D, Grondal C, Vrettou M, Raabe G. Asymmetric synthesis of selectively protected amino sugars and derivatives by a direct organocatalytic Mannich reaction. Angew Chem Int Ed, 2005, 44(26): 4079-4083
44. Connon SJ. The design of novel, synthetically useful (thio) urea-based organo-catalysts. Synlett, 2009, (3): 354-376
45. Yu XH, Wang W. Hydrogen-bond-mediated asymmetric catalysis. Chem Asian J, 2008, 3(3): 516-532
46. Tylor MS, Jacobson EN. Asymmetric catalysis by chiral hydrogen-bond donors. Angew Chem Int Ed, 2006, 45: 1520-1543
47. Connon SJ. Chiral phosphoric acids: Powerful organocatalysts for asymmetric addition reactions to imines. Angew Chem Int Ed, 2006, 45: 3909-3912
48. Takemoto Y. Recognition and activation by ureas and thioureas: Stereoselective reactions using ureas and thioureas as hydrogen-bonding donors. Org Biomol Chem, 2005, 3: 4299-4306
49. Connon SJ. Asymmetric catalysis with bifunctional cinchona alkaloid-based urea and thiourea organocatalysts. Chem Commun, 2008: 2499-2510
50. Doyle AG, Jacobsen EN. Small-molecule H-bond donors in asymmetric catalysis. Chem Rev, 2007, 107(12): 5713-5743
51. Huang HB, Jacobsen EN. Highly enantioselective direct conjugate addition of ketones to nitroalkenes promoted by a chiral primary amine-thiourea catalyst. J Am Chem Soc, 2006, 128(22): 7170-7171
52. Lalonde MP, Chen YG, Jacobsen EN. A chiral primary amine thiourea catalyst for the highly enantioselective direct conjugate addition of α,α-disubstituted aldehydes to nitroalkenes. Angew Chem Int Ed, 2006, 45(38): 6366-6370
53. Akiyama T, Itoh J, Fuchibe K. Recent progress in chiral brønsted acid catalysis. Adv Synth Catal, 2006, 348: 999-1010
54. Wang J, Li H, Yu XH, Zu LS, Wang W. Chiral binaphthyl-derived amine-thiourea organocatalyst-promoted asymmetric Morita-Baylis-Hillman reaction. Org Lett, 2005, 7(19): 4293-4296
55. Li BJ, Jiang L, Liu M, Chen YC, Ding LS, Wu Y. Asymmetric Michael addition of arylthiols to α, β-unsaturated carbonyl compounds catalyzed by bifunctional organocatalysts. Synlett, 2005: 603-606
56. Vakulya B, Varga S, Csámpai A, Soos T. Highly enantioselective conjugate addition of nitromethane to chalcones using bifunctional cinchona organocatalysts. Org Lett, 2005, 7(10): 1967-1969
57. McCooey SH, Connon SJ. Urea- and thiourea-substituted cinchona alkaloid derivatives as highly efficient bifunctional organocatalysts for the aysmmetric addition of malonate to nitroalkenes: Inversion of configuration at C9 dramatically improves catalyst performance. Angew Chem Int Ed, 2005, 44(39): 6367-6370
58. Ye J, Dixon DJ, Hynes PS. Enantioselective organocatalytic Michael addition of malonate esters to nitro olefins using bifunctional cinchonine derivatives. Chem Commun, 2005: 4481-4483
59. Dalko PI, Moisan L. In the golden age of organocatalysis. Angew Chem Int Ed, 2004, 43: 5138-5175
60. Okino T, Hoashi Y, Takemoto Y. Enantioselective Michael reaction of malonates to nitroolefins catalyzed by bifunctional organocatalysts. J Am Chem Soc, 2003, 125(42): 12672-12673
61. Chen Y, McDaid P, Deng L. Asymmetric alcoholysis of cyclic anhydrides. Chem Rev, 2003, 103: 2965-2983
62. France S, Guerin DJ, Miller SJ, Lectka T. Nucleophilic chiral amines as catalysts in asymmetric synthesis. Chem Rev, 2003, 103: 2985-3012
63. Tian SK, Chen YG, Hang JF, Tang L, McDaid P, Deng L. Asymmetric organic catalysis with modified cinchona alkaloids. Acc Chem Res, 2004, 37: 621-631
64. Hang J, Tian SK, 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
65. 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(19): 3321-3324
66. Tang L, Deng L. Dynamic kinetic resolution via dual-function catalysis of modified cinchona alkaloids: Asymmetric synthsis of α-hydroxy carboxylic acids. J Am Chem Soc, 2002, 124: 2870-2871
67. Tian SK, Hong R, Deng L. Catalytic asymmetric cyanosilylation of ketones with chiral Lewis base. J Am Chem Soc, 2003, 125(33): 9900-9901
68. Tian SK, Deng L. A highly enantioselective chiral Lewis base-catalyzed asymmetric cyanation of ketones. J Am Chem Soc, 2001, 123(25): 6195-6196
69. Knudsen KR, Jørgensen KA. A chiral molecular recognition approach to the formation of optically active quaternary centres in aza-Henry reactions. Org Biomol Chem, 2005, 3: 1362-1364
70. Bella M, Jørgensen KA. Organocatalytic enantioselective conjugate addition to alkynones. J Am Chem Soc, 2004, 126(18): 5672-5673
71. Vakulya B, Varga S, Csa'mpai A, Soo's T. Highly enantioselective conjugate sddition of nitromethane to chalcones using bifunctional cinchona organo-catalysts. Org Lett, 2005, 7(10): 1967-1969
72. Li HM, Wang Y, Tang L, Deng L. Highly enantioselective conjugate addition of malonate and β-ketoester to nitroalkenes: Asymmetric C-C bond formation with new bifunctional organic catalysts based on cinchona alkaloids. J Am Chem Soc, 2004, 126(32): 9906-9907
73. Li HM, Song J, Liu XF, Deng L. Catalytic enantioselective C-C bond forming conjugate additions with vinyl sulfones. J Am Chem Soc, 2005, 127(25): 8948-8949
74. Lou S, Taoka BM, Ting A, Schaus SE. Asymmetric Mannich reactions of β-keto esters with acylimines catalyzed by cinchona alkaloids. J Am Chem Soc, 2005, 127(32): 11256-11257
75. Bai S, Liang XP, Song BA, Song BA, Bhadury PS, Hu DY, Yang S. Asymmetric Mannich reactions catalyzed by cinchona alkaloid thiourea enantioselective one-pot synthesis of novel β-amino ester derivatives. Tetrahedron: Asymmetr, 2011, 22(5): 518-523
76. Li L, Song BA, Bhadury PS, Zhang YP, Hu DY, Yang S. Enantioselective synthesis of β-amino esters bearing a benzothiazole moiety via a Mannich-type reaction catalyzed by a cinchona alkaloid derivative. Eur J Org Chem, 2011, (25): 4743-4746
77. Lin P, Song BA, Bhadury PS, Hu DY, Zhang YP, Jin LH, Yang S. Chiral cinchona alkaloid-thiourea catalyzed mannich reaction for enantioselective synthesis of β-amino ketones bearing benzothiazol moiety. Chin J Chem, 2011, 29(11): 2433-2438
78. Kubo K, Shimizu T, Ohyama SI, Murooka H, Iwai A, Nakamura K, Hasegawa K, Kobayashi Y, Takahashi N, Takahashi K, Kato S, Izawa T, Isoe T. Novel potent orally active selective VEGFR-2 tyrosine kinase inhibitors: Synthesis, structure-activity relationships, and antitumor activities of N-phenyl-N′-{4-(4-quinolyloxy) phenyl}ureas. J Med Chem, 2005, 48(5): 1359-1366
79. Wissner A, Floyd MB, Johnson BD, Fraser H, Ingalls C, Nittoli T, Dushin RG, Discafani C, Nilakantan R, Marini J, Ravi M, Cheung KW, Tan XZ, Musto S, Annable T, Siegel MM, Loganzo F. 2-(Quinazolin-4-ylamino)-[1,4]benzoquinones as covalent-binding, irreversible inhibitors of the kinase domain of vascular endothelial growth factor receptor-2. J Med Chem, 2005, 48(24): 7560-7581
80. Baba A, Kawamura N, Makino H, Ohta Y, Taketomi S, Sohda T. Studies on disease-modifying antirheumatic drugs: Synthesis of novel quinoline and quinazoline derivatives and their anti-inflammatory activity. J Med Chem, 1996, 39(26): 5176-5182
81. Farhanullah RVJ, Tripathi BK, Srivastava AK. Synthesis and antihypergl-ycaemic activity of suitably functionalised-4(3H)-quinozolones. Bioorg Med Chem, 2003, 11(11): 2439-2444
82. Pandeya SN, Sriram D, Nath G, Clercq ED. Synthesis, antibacterial, antifungal and anti-HIV evaluation of Schiff and Mannich bases of isatin derivatives with 3-amino-2-methylmercapto quinazolin-4(3H)-one. Pharm Acta Helv, 1999, 74(1): 11-17