Improved conditions for the asymmetric synthesis of α-amino acids using Cinchona-derived anthracenylmethyl ammonium salts as chiral phase-transfer organocatalysts

Tetrahedron Asymmetry

Volumn 17, Issue 24, 2006, Pages 3423-3429

  Chinchilla, Rafael ^a   Nájera, Carmen ^a   Ortega, Francisco J ^a  

^a UNIVERSITY OF ALICANTE   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA AMINO ACID; AMMONIUM DERIVATIVE; ANTHRACENE DERIVATIVE; BASE; BENZOPHENONE DERIVATIVE; CHLOROFORM; FLUOROPHOSPHATE; GLYCINE DERIVATIVE; IMINE; POTASSIUM HYDROXIDE; TOLUENE;

ALKYLATION; ARTICLE; ASYMMETRIC SYNTHESIS; CATALYST; CINCHONA; ENANTIOSELECTIVITY; PHASE TRANSITION; PRIORITY JOURNAL;

EID: 33846644581     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2006.12.004     Document Type: Article

References (105)

1. Williams R.M. Synthesis of Optically Active Amino Acids (1989), Pergamon Press, Oxford
2. Stammer C.H. Tetrahedron 46 (1990) 2231-2254
3. Heimgartner H. Angew. Chem., Int. Ed. Engl. 30 (1991) 238-264
4. Williams R.M., and Hendrix J.A. Chem. Rev. 92 (1992) 889-917
5. Duthaler R.O. Tetrahedron 50 (1994) 1540-1650
6. Burgess K., Ho K.-K., and Mye-Sherman D. Synlett (1994) 575-583
7. Bailey P.D., Clayson J., and Boa A.N. Contemp. Org. Synth. (1995) 173-187
8. North M. Contemp. Org. Synth. (1996) 323-343
9. Studer A. Synthesis (1996) 793-815
10. Seebach D., Sting A.R., and Hoffmann M. Angew. Chem., Int. Ed. 35 (1996) 2708-2748
11. Wirth T. Angew. Chem., Int. Ed. 36 (1997) 225-227
12. Cativiela C., and Díaz-de-Villegas M.D.. Tetrahedron: Asymmetry 9 (1998) 3517-3599
13. Cativiela C., and Díaz-de-Villegas M.D.. Tetrahedron: Asymmetry 11 (2000) 645-732
14. Abellán T., Chinchilla R., Galindo N., Guillena G., Nájera C., and Sansano J.M. Eur. J. Org. Chem. (2000) 2689-2697
15. Nájera C. Synlett (2002) 1388-1403
16. Dehmlow E.V., and Dehmlow S.S. Phase Transfer Catalysis. 3rd ed. (1993), VCH, Weinheim
17. Starks C.M., Liotta C.L., and Halpern M. Phase-Transfer Catalysis (1994), Chapman & Hall, New York
18. In: Sasson Y., and Neumann R. (Eds). Handbook of Phase-Transfer Catalysis (1997), Blackie Academic & Professional, London
19. In: Halpern M.E. (Ed). Phase-Transfer Catalysis. ACS Symposium Series 659 (1997), American Chemical Society, Washington, DC
20. Nelson A. Angew. Chem., Int. Ed. 38 (1999) 1583-1585
21. Makosza M. Pure Appl. Chem. 72 (2000) 1399-1403
22. Kacprzak K., and Gawronski J. Synthesis (2001) 961-998
23. Maruoka K., and Ooi T. Chem. Rev. 103 (2003) 3013-3028
24. Lygo B., and Andrews B.I. Acc. Chem. Res. 37 (2004) 518-525
25. O'Donnell M.J. Acc. Chem. Res. 37 (2004) 506-517
26. Berkessel A., and Gröger H. Asymmetric Organocatalysis (2005), Wiley-VCH, Weinheim
27. O'Donnell M.J., Bennett W.D., and Wu S. J. Am. Chem. Soc. 111 (1989) 2353-2355
28. Lipkowitz K.B., Cavanaugh M.W., Baker B., and O'Donnell M.J. J. Org. Chem. 56 (1991) 5181-5192
29. O'Donnell M.J., and Wu S. Tetrahedron: Asymmetry 3 (1992) 591-594
30. O'Donnell M.J., Wu S., and Huffman J.C. Tetrahedron 50 (1994) 4507-4518
31. O'Donnell M.J., Delgado F., and Pottorf R.S. Tetrahedron 55 (1999) 6347-6362
32. O'Donnell M.J. Aldrichim. Acta 34 (2001) 3-15
33. Lygo B., and Wainwright P.G. Tetrahedron Lett. 38 (1997) 8595-8598
34. Lygo B., Crosby J., and Peterson J.A. Tetrahedron Lett. 40 (1999) 1385-1388
35. Lygo B. Tetrahedron Lett. 40 (1999) 1389-1392
36. Lygo B., Crosby J., and Peterson J.A. Tetrahedron Lett. 40 (1999) 8671-8674
37. Lygo B., Crosby J., Lowdon T.R., Peterson J.A., and Wainwright P.G. Tetrahedron 57 (2001) 2403-2409
38. Lygo B., Andrews B.I., Crosby J., and Peterson J.A. Tetrahedron Lett. 43 (2002) 8015-8018
39. Lygo B., and Allbutt B. Synlett (2004) 326-328
40. Corey E.J., Xu F., and Noe M.C. J. Am. Chem. Soc. 119 (1997) 12414-12415
41. Corey E.J., Noe M.C., and Xu F. Tetrahedron Lett. 39 (1998) 5347-5350
42. Horikawa M., Busch-Petersen J., and Corey E.J. Tetrahedron Lett. 40 (1999) 3843-3846
43. Jew S., Jeong B., Yoo M., Huh H., and Park H. Chem. Commun. (2001) 1244-1245
44. Park H., Jeong B., Yoo M., Lee J., Park M., Lee Y., Kim M., and Jew S. Angew. Chem., Int. Ed. 41 (2002) 3036-3038
45. Chinchilla R., Mazón P., and Nájera C. Tetrahedron: Asymmetry 13 (2002) 927-931
46. Park H., Jeong B., Yoo M., Lee J., Park B., Kim M., and Jew S. Tetrahedron Lett. 44 (2003) 3497-3500
47. Siva A., and Murugan E. J. Mol. Catal. A: Chem. 241 (2005) 111-117
48. Park H., Jeong B., Yoo M., Park M., Huh H., and Jew S. Tetrahedron Lett. 42 (2001) 4645-4648
49. Siva A., and Murugan E. Synthesis (2005) 2927-2933
50. Mazón P., Chinchilla R., Nájera C., Guillena G., Kreiter R., Klein Gebbink R.J.M., and van Koten G. Tetrahedron: Asymmetry 13 (2002) 2181-2185
51. Guillena G., Kreiter R., van de Coevering R., Klein Gebbink R.J.M., van Koten G., Mazón P., Chinchilla R., and Nájera C. Tetrahedron: Asymmetry 14 (2003) 3705-3712
52. Yongmei W., Zhengpu Z., Zhen W., Jiben M., and Hodge P. Chin. J. Polym. Sci. 16 (1998) 356-361
53. Zhengpu Z., Yongmei W., Zhen W., and Hodge P. React. Funct. Polym. 41 (1999) 37-43
54. Chinchilla R., Mazón P., and Nájera C. Tetrahedron: Asymmetry 11 (2000) 3277-3281
55. Thierry B., Plaquevent J.-C., and Cahard D. Tetrahedron: Asymmetry 12 (2001) 983-986
56. Thierry B., Perrard T., Audouard C., Plaquevent J.-C., and Cahard D. Synthesis (2001) 1742-1746
57. Thierry B., Plaquevent J.-C., and Cahard D. Tetrahedron: Asymmetry 14 (2003) 1671-1677
58. Danelli T., Annunziata R., Benaglia M., Cinquini M., Cozzi F., and Tocco G. Tetrahedron: Asymmetry 14 (2003) 461-467
59. Chinchilla R., Mazón P., and Nájera C. Molecules 9 (2004) 349-364
60. Chinchilla R., Mazón P., and Nájera C. Adv. Synth. Catal. 346 (2004) 1186-1194
61. Ooi T., Kameda M., and Maruoka K. J. Am. Chem. Soc. 121 (1999) 6519-6520
62. Ooi T., Tayama E., Doda K., Takeuchi M., and Maruoka K. Synlett (2000) 1500-1502
63. Ooi T., Takeuchi M., Kameda M., and Maruoka K. J. Am. Chem. Soc. 122 (2000) 5228-5229
64. Ooi T., Uematsu Y., and Maruoka K. Adv. Synth. Catal. 344 (2002) 288-291
65. Ooi T., Uematsu Y., and Maruoka K. Tetrahedron Lett. 45 (2004) 1675-1678
66. Kano T., Konishi S., Shirakawa S., and Maruoka K. Tetrahedron: Asymmetry 15 (2004) 1243-1245
67. Shirakawa S., Yamamoto K., Kitamura M., Ooi T., and Maruoka K. Angew. Chem., Int. Ed. 44 (2005) 625-628
68. Kitamura M., Shirakawa S., and Maruoka K. Angew. Chem., Int. Ed. 44 (2005) 1549-1551
69. Han Z., Yamaguchi Y., Kitamura M., and Maruoka K. Tetrahedron Lett. 46 (2005) 8555-8558
70. Ooi T., Takeuchi M., Kato D., Uematsu Y., Yamada E., Sakai D., and Maruoka K. J. Am. Chem. Soc. 127 (2005) 5073-5083
71. Manabe K. Tetrahedron Lett. 39 (1998) 5807-5810
72. Manabe K. Tetrahedron 54 (1998) 14456-14476
73. Belokon' Y.N., Kotchetkov K.A., Churkina T.D., Ikonnikov N.S., Chesnokov A.A., Larionov A.V., Parmár V.S., Kumar R., and Kagan H.B. Tetrahedron: Asymmetry 9 (1998) 851-857
74. Belokon' Y.N., Kotchetkov K.A., Churkina T.D., Ikonnikov N.S., Chesnokov A.A., Larionov A.V., Singh I., Parmár V.S., Vyskocil S., and Kagan H.B. J. Org. Chem. 65 (2000) 7041-7048
75. Shibuguchi T., Fukuta Y., Akachi Y., Sekine A., Oshima T., and Shibasaki M. Tetrahedron Lett. 43 (2002) 9539-9543
76. Arai S., Tsuji R., and Nishida A. Tetrahedron Lett. 43 (2002) 9535-9537
77. Kowtoniuk W.E., MacFarland D.K., and Grover G.N. Tetrahedron Lett. 46 (2005) 5703-5705
78. Kita T., Georgieva A., Hashimoto Y., Nakata T., and Nagasawa K. Angew. Chem., Int. Ed. 41 (2002) 2832-2834
79. Belokon' Y.N., Kotchetkov K.A., Churkina T.D., Ikonnikov N.S., Vyskocil S., and Kagan H.B. Tetrahedron: Asymmetry 10 (1999) 1723-1728
80. Belokon' Y.N., Kotchetkov K.A., Churkina T.D., Ikonnikov N.S., Larionov O.V., Harutyunyan S.R., Vyskocil S., North M., and Kagan H.B. Angew Chem., Int. Ed. 40 (2001) 1948-1951
81. Casas J., Nájera C., Sansano J.M., González J., Saá J.M., and Vega M. Tetrahedron: Asymmetry 12 (2001) 699-702
82. Belokon' Y.N., North M., Kublitski V.S., Ikonnikov N.S., Krasik P.E., and Maleev V.L. Tetrahedron Lett. 40 (1999) 6105-6108
83. Belokon' Y.N., Davies R.G., and North M. Tetrahedron Lett. 41 (2000) 7245-7248
84. Belokon' Y.N., Bhave D., D'Addario D., Groaz E., North M., and Tagliazucca V. Tetrahedron 60 (2004) 1849-1861
85. Jotterand N., Pearce D.A., and Imperiali B. J. Org. Chem. 66 (2001) 3224-3228
86. Boisnard S., Carbonnelle A.-C., and Zhu J. Org. Lett. 3 (2001) 2061-2064
87. Boeckmann Jr. R.K., Clark T.J., and Shook B.C. Org. Lett. 4 (2002) 2109-2112
88. Berthelot A., Piguel S., Le Dour G., and Vidal J. J. Org. Chem. 68 (2003) 9835-9838
89. Shults M.D., Pearce D.A., and Imperiali B. J. Am. Chem. Soc. 125 (2003) 10591-10597
90. Armstrong A., and Scutt J.N. Chem. Commun. (2004) 510-511
91. De Paolis M., Chen X., and Zhu J. Synlett (2004) 729-731
92. Lin L.S., Lanza T.J., Castonguay L.A., Kamenecka T., McCauley E., Van Riper G., Egger L.A., Mumford R.A., Tong X., MacCoss M., Schmidt J.A., and Hagmann W.K. Bioorg. Med. Chem. Lett. 14 (2004) 2331-2334
93. Srinivasan J.M., Burks H.E., Smith C.R., Viswanathan R., and Johnston J.N. Synthesis (2005) 330-333
94. Chen X., Chen J., De Paolis M., and Zhu J. J. Org. Chem. 70 (2005) 4397-4408
95. Lepine R., and Zhu J. Org. Lett. 7 (2005) 2981-2984
96. Van Rompaey K., Ballet S., Tomboly C., De Wachter R., Vanommeslaeghe K., Biesemans M., Willem R., and Tourwe D. Eur. J. Org. Chem. (2006) 2899-2911
97. Couturier C., Schlama T., and Zhu J. Synlett (2006) 1691-1694
98. Ohshima T., Gnanadesikan V., Shibuguchi T., Fukuta Y., Nemoto T., and Shibasaki M. J. Am. Chem. Soc. 125 (2003) 11206-11207
99. Ohshima T., Shibuguchi T., Fukuta Y., and Shibasaki M. Tetrahedron 60 (2004) 7743-7754
100. Chinchilla R., Mazón P., Nájera C., and Ortega F.J. Tetrahedron: Asymmetry 15 (2004) 2603-2607
101. Chinchilla R., Mazón P., Nájera C., and Ortega F.J. Arkivoc vi (2005) 222-232
102. Lygo B., and Andrews B.I. Tetrahedron Lett. 44 (2003) 4499-4502
103. Hulin B., and Lopaze M.G. Tetrahedron: Asymmetry 15 (2004) 1957-1958
104. Oppolzer W., Moretti R., and Zhou C. Helv. Chim. Acta 77 (1994) 2363-2380
105. 2O). Dictionary of Organic Compounds (1982), Chapman & Hall, New York