Subscribe to RSS
DOI: 10.1055/s-0031-1289756
Recent Advances in the Asymmetric Synthesis of α-(Trifluoromethyl)-Containing α-Amino Acids
Publication History
Received: 20 February 2012
Accepted after revision: 20 March 2012
Publication Date:
27 April 2012 (online)
Abstract
This review article provides a comprehensive update on the development of new methods for the asymmetric synthesis of α-(trifluoromethyl)-α-amino acids, covering the literature from 2006 to mid-February 2012. Most of the methods discussed are based on asymmetric additions across the carbon–nitrogen double bond of the imines derived from esters of 3,3,3-trifluoropyruvic acid. Medium to high levels of stereocontrol can be achieved using phenylglycinol-derived chiral auxiliaries attached to the nitrogen of the corresponding imines. Among the enantioselective approaches, impressive results were achieved through the application of the Strecker reaction using chiral thioureas, as well as chiral Brønsted acids, as organocatalysts.
1 Introduction
2 Stoichiometric Asymmetric Syntheses of α-(Trifluoromethyl)-α-amino Acids
3 Catalytic Asymmetric Syntheses of α-(Trifluoromethyl)-α-amino Acids
4 Miscellaneous
5 Conclusions
-
References
- 1a Ohfune Y, Shinada T. Eur. J. Org. Chem. 2005; 5127
- 1b Nájera C, Sansano JM. Chem. Rev. 2007; 107: 4584
- 1c Vogt H, Bräse S. Org. Biomol. Chem. 2007; 5: 406
- 1d Cativiela C, Díaz-de-Villegas MD. Tetrahedron: Asymmetry 2007; 18: 569
- 1e Maity P, König B. Biopolymers (Pept. Sci.) 2008; 90: 8
- 1f Cativiela C, Ordóñez M. Tetrahedron: Asymmetry 2009; 20: 1
- 1g Soloshonok VA, Sorochinsky AE. Synthesis 2010; 2319
- 2a Soloshonok VA, Tang X, Hruby VJ, Meervelt LV. Org. Lett. 2001; 3: 341
- 2b Ellis TK, Martin CH, Ueki H, Soloshonok VA. Tetrahedron Lett. 2003; 44: 1063
- 2c Ellis TK, Hochla VM, Soloshonok VA. J. Org. Chem. 2003; 68: 4973
- 2d Ellis TK, Martin CH, Tsai GM, Ueki H, Soloshonok VA. J. Org. Chem. 2003; 68: 6208
- 2e Ellis TK, Ueki H, Yamada T, Ohfune Y, Soloshonok VA. J. Org. Chem. 2006; 71: 8572
- 2f Soloshonok VA, Boettiger TU, Bolene SB. Synthesis 2008; 2594
- 3 For a review on sterically constrained α�-amino acids, see: Soloshonok VA. Curr. Org. Chem. 2002; 6: 341
- 4a Toniolo C, Crisma M, Formaggio F, Peggion C. Biopolymers (Pept. Sci.) 2001; 60: 396
- 4b Toniolo C, Formaggio F, Kaptein B, Broxterman QB. Synlett 2006; 1295
- 5a Bravo P, Farina A, Frigerio M, Valdo Meille S, Viani F, Soloshonok VA. Tetrahedron: Asymmetry 1994; 5: 987
- 5b Soloshonok VA, Kirilenko AG, Fokina NA, Galushko SV, Kukhar VP, Svedas VK, Resnati G. Tetrahedron: Asymmetry 1994; 5: 1225
- 5c Soloshonok VA, Avilov DV, Kukhar VP. Tetrahedron: Asymmetry 1996; 7: 1547
- 6a Soloshonok VA, Hayashi T, Ishikawa K, Nagashima N. Tetrahedron Lett. 1994; 35: 1055
- 6b Soloshonok VA, Kacharov AD, Hayashi T. Tetrahedron 1996; 52: 245
- 6c Soloshonok VA, Kacharov AD, Avilov DV, Hayashi T. Tetrahedron Lett. 1996; 37: 7845
- 8 Maisch D, Wadhwani P, Afonin S, Böttcher C, Koksch B, Ulrich AS. J. Am. Chem. Soc. 2009; 131: 15596
- 9 Kobzev SV, Soloshonok VA, Galushko SV, Yagupolskii YL, Kukhar VP. Zh. Obshch. Khim. 1989; 59: 909
- 10a Koksch B, Sewald N, Hofmann H.-J, Burger K, Jakubke H.-D. J. Pept. Sci. 1997; 3: 157
- 10b Koksch B, Quaedflieg PJ. L. M, Michel T, Burger K, Broxterman QB, Schoemaker HE. Tetrahedron: Asymmetry 2004; 15: 1401
- 10c 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
- 10d Chaume G, Lensen N, Caupène C, Brigaud T. Eur. J. Org. Chem. 2009; 5717
- 11a Kukhar VP, Yagupolskii YL, Soloshonok VA. Russ. Chem. Rev. 1990; 59: 89
- 11b Kukhar VP, Soloshonok VA. Russ. Chem. Rev. 1991; 60: 850
- 11c Sutherland A, Willis CL. Nat. Prod. Rep. 2000; 17: 621
- 11d Qiu X.-L, Meng W.-D, Qing F.-L. Tetrahedron 2004; 60: 6711
- 11e Kukhar VP, Sorochinsky AE, Soloshonok VA. Future Med. Chem. 2009; 1: 793
- 11f Sorochinsky AE, Soloshonok VA. J. Fluorine Chem. 2010; 131: 127
- 11g Czekelius C, Tzschucke CC. Synthesis 2010; 543
- 11h Tarui A, Sato K, Omote M, Kumadaki I, Ando A. Adv. Synth. Catal. 2010; 352: 2733
- 11i Qiu X.-L, Qing F.-L. Eur. J. Org. Chem. 2011; 3261
- 11j Mikami K, Fustero S, Sánchez-Roselló M, Aceña JL, Soloshonok VA, Sorochinsky AE. Synthesis 2011; 3045
- 12 Smits R, Cadicamo CD, Burger K, Koksch B. Chem. Soc. Rev. 2008; 37: 1727
- 13a Bégué J.-P, Bonnet-Delpon D, Crousse B, Legros J. Chem. Soc. Rev. 2005; 34: 562
- 13b Fustero S, Sanz-Cervera JF, Aceña JL, Sánchez-Roselló M. Synlett 2009; 525
- 13c Nie J, Guo H.-C, Cahard D, Ma J.-A. Chem. Rev. 2011; 111: 455
- 14a Soloshonok VA, Gerus II, Yagupolskii YL. Zh. Org. Khim. 1986; 22: 1335
- 14b Soloshonok VA, Gerus II, Yagupolskii YL, Kukhar VP. Zh. Org. Khim. 1987; 23: 2308
- 14c Soloshonok VA, Yagupolskii YL, Kukhar VP. Zh. Org. Khim. 1988; 24: 1638
- 14d Soloshonok VA, Kukhar VP. Zh. Org. Khim. 1990; 26: 419
- 15 Osipov SN, Chkanikov ND, Kolomiets AF, Fokin AV. Izv. Akad. Nauk SSSR, Ser. Khim. 1986; 1384
- 16a Ohkura H, Berbasov DO, Soloshonok VA. Tetrahedron 2003; 59: 1647
- 16b Berbasov DO, Ojemaye ID, Soloshonok VA. J. Fluorine Chem. 2004; 125: 603
- 17a Tamura K, Mizukami H, Maeda K, Watanabe H, Uneyama K. J. Org. Chem. 1993; 58: 32
- 17b Uneyama K. J. Fluorine Chem. 1999; 97: 11
- 18a Bravo P, Capelli S, Meille SV, Viani F, Zanda M, Kukhar VP, Soloshonok VA. Tetrahedron: Asymmetry 1994; 5: 2009
- 18b Bravo P, Viani F, Zanda M, Kukhar VP, Soloshonok VA, Fokina NA, Shishkin OV, Struchkov YT. Gazz. Chim. Ital. 1996; 126: 645
- 19 Asensio A, Bravo P, Crucianelli M, Farina A, Fustero S, García Soler J, Meille SV, Panzeri W, Viani F, Volonterio A, Zanda M. Eur. J. Org. Chem. 2001; 1449
- 20 Rassukana YV, Khomutnyk YY, Synytsya AD, Onys’ko PP. Phosphorus, Sulfur Silicon Relat. Elem. 2011; 186: 718
- 21 Abid M, Teixeira L, Török B. Org. Lett. 2008; 10: 933
- 22a Soloshonok VA, Kirilenko AG, Kukhar VP, Resnati G. Tetrahedron Lett. 1993; 34: 3621
- 22b Soloshonok VA, Ono T. Tetrahedron 1996; 52: 14701
- 22c Soloshonok VA, Kukhar VP. Tetrahedron 1997; 53: 8307
- 23 Min Q.-Q, He C.-Y, Zhou H, Zhang X. Chem. Commun. 2010; 46: 8029
- 24 Yang J, Min Q.-Q, He Y, Zhang X. Tetrahedron Lett. 2011; 52: 4675
- 25 Chaume G, Van Severen M.-C, Marinkovic S, Brigaud T. Org. Lett. 2006; 8: 6123
- 26 Caupène C, Chaume G, Ricard L, Brigaud T. Org. Lett. 2009; 11: 209
- 27 Huguenot F, Billac A, Brigaud T, Portella C. J. Org. Chem. 2008; 73: 2564
- 28 Simon J, Nguyen TT, Chelain E, Lensen N, Pytkowicz J, Chaume G, Brigaud T. Tetrahedron: Asymmetry 2011; 22: 309
- 29 Fustero S, Sánchez-Roselló M, Báez C, del Pozo C, García Ruano JL, Alemán J, Marzo L, Parra A. Amino Acids 2011; 41: 559
- 30a Fustero S, Sánchez-Roselló M, Rodrigo V, del Pozo C, Sanz-Cervera JF, Simón A. Org. Lett. 2006; 8: 4129
- 30b Fustero S, Sánchez-Roselló M, Rodrigo V, Sanz-Cervera JF, Piera J, Simón-Fuentes A, del Pozo C. Chem.–Eur. J. 2008; 14: 7019
- 30c Fustero S, Rodrigo V, Sánchez-Roselló M, Mojarrad F, Vicedo A, Moscardó T, del Pozo C. J. Fluorine Chem. 2008; 129: 943
- 31 Fustero S, Rodrigo V, Sánchez-Roselló M, del Pozo C, Timoneda J, Frizler M, Sisay MT, Bajorath J, Calle LP, Cañada FJ, Jiménez-Barbero J, Gütschow M. Chem.–Eur. J. 2011; 17: 5256
- 32 Zhan F, Liu Z.-J, Liu J.-T. Org. Biomol. Chem. 2011; 9: 3625
- 33 Liu J, Hu J. Chem.–Eur. J. 2010; 16: 11443
- 34a Levin VV, Dilman AD, Belyakov PA, Struchkova MI, Tartakovsky VA. Eur. J. Org. Chem. 2008; 5226
- 34b Shevchenko NE, Vlasov K, Nenajdenko VG, Röschenthaler G.-V. Tetrahedron 2011; 67: 69
- 35a Fustero S, Albert L, Aceña JL, Sanz-Cervera JF, Asensio A. Org. Lett. 2008; 10: 605
- 35b Fustero S, Albert L, Mateu N, Chiva G, Miró J, González J, Aceña JL. Chem.–Eur. J. 2012; 18: 3753
- 36 Katagiri T, Katayama Y, Taeda M, Ohshima T, Iguchi N, Uneyama K. J. Org. Chem. 2011; 76: 9305
- 37 Enders D, Gottfried K, Raabe G. Adv. Synth. Catal. 2010; 352: 3147
- 38 Liu Y.-L, Shi T.-D, Zhou F, Zhao X.-L, Wang X, Zhou J. Org. Lett. 2011; 13: 3826
- 39 Kim SY, Kim SJ, Jang DO. Chem.–Eur. J. 2010; 16: 13046
- 40 Husmann R, Sugiono E, Mersmann S, Raabe G, Rueping M, Bolm C. Org. Lett. 2011; 13: 1044
- 41a SDE via achiral chromatography, see: Soloshonok VA, Berbasov DO. J. Fluorine Chem. 2006; 127: 597
- 41b SDE via sublimation, see: Ueki H, Yasumoto M, Soloshonok VA. Tetrahedron: Asymmetry 2010; 21: 1396
- 42a Soloshonok VA, Berbasov DO. Chim. Oggi/Chemistry Today 2006; 24: 44
- 42b Soloshonok VA. Angew. Chem. Int. Ed. 2006; 45: 766
- 43 Huang G, Yang J, Zhang X. Chem. Commun. 2011; 47: 5587
- 44a Shchetnikov GT, Zotova MA, Bruneau C, Dixneuf PH, Osipov SN. Eur. J. Org. Chem. 2010; 1587
- 44b Vorobyeva DV, Mailyan AK, Peregudov AS, Karimova NM, Vasilyeva TP, Bushmarinov IS, Bruneau C, Dixneuf PH, Osipov SN. Tetrahedron 2011; 67: 3524
- 44c Mailyan AK, Krylov IM, Bruneau C, Dixneuf PH, Osipov SN. Synlett 2011; 2321
- 44d Eckert M, Moulin S, Monnier F, Titanyuk ID, Osipov SN, Roisnel T, Dérien S, Dixneuf PH. Chem.–Eur. J. 2011; 17: 9456
- 44e Vorobyeva DV, Sokolova NV, Nenajdenko VG, Peregudov AS, Osipov SN. Tetrahedron 2012; 68: 872
- 45a Gulevich AV, Shevchenko NE, Balenkova ES, Röschenthaler G.-V, Nenajdenko VG. Synlett 2009; 403
- 45b Pajkert R, Röschenthaler G.-V. J. Fluorine Chem. 2010; 131: 1362
- 45c Vorobyeva DV, Karimova NM, Odinets IL, Röschenthaler G.-V, Osipov SN. Org. Biomol. Chem. 2011; 9: 7335
- 46 Palacios F, Ochoa de Retana AM, Pascual S, Fernández de Trocóniz G. Tetrahedron 2011; 67: 1575
- 47 Martin T, Massif C, Wermester N, Linol J, Tisse S, Cardinael P, Coquerel G, Bouillon J.-P. Tetrahedron: Asymmetry 2011; 22: 12
For recent reviews, see:
For recent papers, see: