Recent advances in the asymmetric synthesis of α-(trifluoromethyl)- containing α-amino acids

Synthesis (Germany)

Volumn 44, Issue 11, 2012, Pages 1591-1602

  Aceña, José Luis ^a   Sorochinsky, Alexander E ^a,b,c   Soloshonok, Vadim A ^a,b  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

^b BASQUE FOUNDATION FOR SCIENCE   (Spain)

^c INSTITUTE OF BIOORGANIC CHEMISTRY AND PETROCHEMISTRY   (Ukraine)

Author keywords

amino acids; asymmetric synthesis; catalysis; chiral auxiliaries; fluorine

Indexed keywords

ASYMMETRIC ADDITION; ASYMMETRIC SYNTHESIS; CHIRAL AUXILIARIES; DOUBLE BONDS; ENANTIOSELECTIVE APPROACH; ORGANOCATALYSTS; STEREOCONTROL; STRECKER REACTIONS; TRIFLUOROMETHYL;

CATALYSIS; FLUORINE; NITROGEN COMPOUNDS; THIOUREAS;

AMINO ACIDS;

ALPHA (TRIFLUOROMETHYL)ALPHA AMINO ACID; ALPHA AMINO ACID; CARBON; NITROGEN; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CARBON NITROGEN RATIO; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOSELECTIVITY; STEREOCHEMISTRY; STOICHIOMETRY; STRECKER REACTION;

EID: 84861340319     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0031-1289756     Document Type: Article

References (72)

1. Ohfune Y, Shinada T. Eur. J. Org. Chem.: 2005; 5127
2. Njera C, Sansano JM. Chem. Rev.: 2007; 107 4584
3. Vogt H, Bräse S. Org. Biomol. Chem.: 2007; 5 406
4. Cativiela C, Daz-de-Villegas MD. Tetrahedron: Asymmetry: 2007; 18 569
5. Maity P, König B. Biopolymers (Pept. Sci.): 2008; 90 8
6. Cativiela C, Ordez M. Tetrahedron: Asymmetry: 2009; 20 1
7. Soloshonok VA, Sorochinsky AE. Synthesis: 2010; 2319
8. Soloshonok VA, Tang X, Hruby VJ, Meervelt LV. Org. Lett.: 2001; 3 341
9. Ellis TK, Martin CH, Ueki H, Soloshonok VA. Tetrahedron Lett.: 2003; 44 1063
10. Ellis TK, Hochla VM, Soloshonok VA. J. Org. Chem.: 2003; 68 4973
11. Ellis TK, Martin CH, Tsai GM, Ueki H, Soloshonok VA. J. Org. Chem.: 2003; 68 6208
12. Ellis TK, Ueki H, Yamada T, Ohfune Y, Soloshonok VA. J. Org. Chem.: 2006; 71 8572
13. Soloshonok VA, Boettiger TU, Bolene SB. Synthesis: 2008; 2594
14. Toniolo C, Crisma M, Formaggio F, Peggion C. Biopolymers (Pept. Sci.): 2001; 60 396
15. Toniolo C, Formaggio F, Kaptein B, Broxterman QB. Synlett: 2006; 1295
16. Bravo P, Farina A, Frigerio M, Valdo Meille S, Viani F, Soloshonok VA. Tetrahedron: Asymmetry: 1994; 5 987
17. Soloshonok VA, Kirilenko AG, Fokina NA, Galushko SV, Kukhar VP, Svedas VK, Resnati G. Tetrahedron: Asymmetry: 1994; 5 1225
18. Soloshonok VA, Avilov DV, Kukhar VP. Tetrahedron: Asymmetry: 1996; 7 1547
19. Soloshonok VA, Hayashi T, Ishikawa K, Nagashima N. Tetrahedron Lett.: 1994; 35 1055
20. Soloshonok VA, Kacharov AD, Hayashi T. Tetrahedron: 1996; 52 245
21. Soloshonok VA, Kacharov AD, Avilov DV, Hayashi T. Tetrahedron Lett.: 1996; 37 7845
22. Zanda M. New J. Chem.: 2004; 28 1401
23. Smits R, Koksch B. Curr. Top. Med. Chem.: 2006; 6 1483
24. Koksch B, Sewald N, Hofmann H.-J, Burger K, Jakubke H.-D. J. Pept. Sci.: 1997; 3 157
25. Koksch B, Quaedflieg PJ. L. M, Michel T, Burger K, Broxterman QB, Schoemaker HE. Tetrahedron: Asymmetry: 2004; 15 1401
26. Dal Pozzo A, Ni M, Muzi L, de Castiglione R, Mondelli R, Mazzini S, Penco S, Pisano C, Castorina M, Giannini G. J. Med. Chem.: 2006; 49 1808
27. Chaume G, Lensen N, Caupne C, Brigaud T. Eur. J. Org. Chem.: 2009; 5717
28. Kukhar VP, Yagupolskii YL, Soloshonok VA. Russ. Chem. Rev.: 1990; 59 89
29. Kukhar VP, Soloshonok VA. Russ. Chem. Rev.: 1991; 60 850
30. Sutherland A, Willis CL. Nat. Prod. Rep.: 2000; 17 621
31. Qiu X.-L, Meng W.-D, Qing F.-L. Tetrahedron: 2004; 60 6711
32. Kukhar VP, Sorochinsky AE, Soloshonok VA. Future Med. Chem.: 2009; 1 793
33. Sorochinsky AE, Soloshonok VA. J. Fluorine Chem.: 2010; 131 127
34. Czekelius C, Tzschucke CC. Synthesis: 2010; 543
35. Tarui A, Sato K, Omote M, Kumadaki I, Ando A. Adv. Synth. Catal.: 2010; 352 2733
36. Qiu X.-L, Qing F.-L. Eur. J. Org. Chem.: 2011; 3261
37. Mikami K, Fustero S, Snchez-Rosell M, Acea JL, Soloshonok VA, Sorochinsky AE. Synthesis: 2011; 3045
38. Bgu J.-P, Bonnet-Delpon D, Crousse B, Legros J. Chem. Soc. Rev.: 2005; 34 562
39. Fustero S, Sanz-Cervera JF, Acea JL, Snchez-Rosell M. Synlett: 2009; 525
40. Nie J, Guo H.-C, Cahard D, Ma J.-A. Chem. Rev.: 2011; 111 455
41. Soloshonok VA, Gerus II, Yagupolskii YL. Zh. Org. Khim.: 1986; 22 1335
42. Soloshonok VA, Gerus II, Yagupolskii YL, Kukhar VP. Zh. Org. Khim.: 1987; 23 2308
43. Soloshonok VA, Yagupolskii YL, Kukhar VP. Zh. Org. Khim.: 1988; 24 1638
44. Soloshonok VA, Kukhar VP. Zh. Org. Khim.: 1990; 26 419
45. Ohkura H, Berbasov DO, Soloshonok VA. Tetrahedron: 2003; 59 1647
46. Berbasov DO, Ojemaye ID, Soloshonok VA. J. Fluorine Chem.: 2004; 125 603
47. Tamura K, Mizukami H, Maeda K, Watanabe H, Uneyama K. J. Org. Chem.: 1993; 58 32
48. Uneyama K. J. Fluorine Chem.: 1999; 97 11
49. Bravo P, Capelli S, Meille SV, Viani F, Zanda M, Kukhar VP, Soloshonok VA. Tetrahedron: Asymmetry: 1994; 5 2009
50. Bravo P, Viani F, Zanda M, Kukhar VP, Soloshonok VA, Fokina NA, Shishkin OV, Struchkov YT. Gazz. Chim. Ital.: 1996; 126 645
51. Soloshonok VA, Kirilenko AG, Kukhar VP, Resnati G. Tetrahedron Lett.: 1993; 34 3621
52. Soloshonok VA, Ono T. Tetrahedron: 1996; 52 14701
53. Soloshonok VA, Kukhar VP. Tetrahedron: 1997; 53 8307
54. Fustero S, Snchez-Rosell M, Rodrigo V, del Pozo C, Sanz-Cervera JF, Simn A. Org. Lett.: 2006; 8 4129
55. Fustero S, Snchez-Rosell M, Rodrigo V, Sanz-Cervera JF, Piera J, Simn-Fuentes A, del Pozo C. Chem.-Eur. J.: 2008; 14 7019
56. Fustero S, Rodrigo V, Snchez-Rosell M, Mojarrad F, Vicedo A, Moscard T, del Pozo C. J. Fluorine Chem.: 2008; 129 943
57. Levin VV, Dilman AD, Belyakov PA, Struchkova MI, Tartakovsky VA. Eur. J. Org. Chem.: 2008; 5226
58. Shevchenko NE, Vlasov K, Nenajdenko VG, Röschenthaler G.-V. Tetrahedron: 2011; 67 69
59. Fustero S, Albert L, Acea JL, Sanz-Cervera JF, Asensio A. Org. Lett.: 2008; 10 605
60. Fustero S, Albert L, Mateu N, Chiva G, Mir J, Gonzlez J, Acea JL. Chem.-Eur. J.: 2012; 18 3753
61. SDE via achiral chromatography, see: Soloshonok VA, Berbasov DO. J. Fluorine Chem.: 2006; 127 597
62. SDE via sublimation, see: Ueki H, Yasumoto M, Soloshonok VA. Tetrahedron: Asymmetry: 2010; 21 1396
63. Soloshonok VA, Berbasov DO. Chim. Oggi/Chemistry Today: 2006; 24 44
64. Soloshonok VA. Angew. Chem. Int. Ed.: 2006; 45 766
65. Shchetnikov GT, Zotova MA, Bruneau C, Dixneuf PH, Osipov SN. Eur. J. Org. Chem.: 2010; 1587
66. Vorobyeva DV, Mailyan AK, Peregudov AS, Karimova NM, Vasilyeva TP, Bushmarinov IS, Bruneau C, Dixneuf PH, Osipov SN. Tetrahedron: 2011; 67 3524
67. Mailyan AK, Krylov IM, Bruneau C, Dixneuf PH, Osipov SN. Synlett: 2011; 2321
68. Eckert M, Moulin S, Monnier F, Titanyuk ID, Osipov SN, Roisnel T, Drien S, Dixneuf PH. Chem.-Eur. J.: 2011; 17 9456
69. Vorobyeva DV, Sokolova NV, Nenajdenko VG, Peregudov AS, Osipov SN. Tetrahedron: 2012; 68 872
70. Gulevich AV, Shevchenko NE, Balenkova ES, Röschenthaler G.-V, Nenajdenko VG. Synlett: 2009; 403
71. Pajkert R, Röschenthaler G.-V. J. Fluorine Chem.: 2010; 131 1362
72. Vorobyeva DV, Karimova NM, Odinets IL, Röschenthaler G.-V, Osipov SN. Org. Biomol. Chem.: 2011; 9 7335