Catalytic enantioselective synthesis of N,Cα,Cα-trisubstituted α-amino acid derivatives using 1H-imidazol-4(5H)-ones as key templates

Angewandte Chemie - International Edition

Volumn 54, Issue 23, 2015, Pages 6883-6886

  Etxabe, Julen ^a   Izquierdo, Joseba ^a   Landa, Aitor ^a   Oiarbide, Mikel ^a   Palomo, Claudio ^a  

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

Author keywords

amino acids; asymmetric catalysis; Michael additions; organocatalysis; synthetic methods

Indexed keywords

ADDITION REACTIONS; CATALYSIS; CHELATION; ENANTIOSELECTIVITY; SUBSTITUTION REACTIONS;

ASYMMETRIC CATALYSIS; ASYMMETRIC SYNTHESIS; EFFICIENT CONSTRUCTION; ELECTRON WITHDRAWING GROUP; ENANTIOSELECTIVE SYNTHESIS; MICHAEL ADDITIONS; ORGANOCATALYSIS; SYNTHETIC METHODS;

AMINO ACIDS;

AMINO ACID; IMIDAZOLE DERIVATIVE;

CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

AMINO ACIDS; CATALYSIS; IMIDAZOLES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 84930505886     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201501275     Document Type: Article

References (50)

1. Amino Acids, Peptides and Proteins in Organic Chemistry, Vols. 1&2 (Ed.:, A. B. Hughes,), Wiley-VCH, Weinheim, 2009.
2. C. Cativiela, M. D. Díaz de Villegas, Tetrahedron: Asymmetry 2007, 18, 569-623
3. C. Cativiela, M. Ordoñez, Tetrahedron: Asymmetry 2009, 20, 1-63
4. Y. Ohfune, T. Shinada, Eur. J. Org. Chem. 2005, 5127-5143
5. H. Vogt, S. Bräse, Org. Biomol. Chem. 2007, 5, 406-430
6. R. A. Monsey, J. S. Fisk, J. J. Tepe, Tetrahedron: Asymmetry 2008, 19, 2755-2762
7. K. Bera, I. N. N. Namboothiri, Asian J. Org. Chem. 2014, 3, 1234-1260.
8. C. Nájera, J. M. Sansano, Chem. Rev. 2007, 107, 4584-4671
9. A. E. Metz, M. C. Kozlowski, J. Org. Chem. 2015, 80, 1-7.
10. J. S. Fisk, R. A. Monsey, J. J. Tepe, Chem. Soc. Rev. 2007, 36, 1432-1440
11. A.-N. R. Alba, R. Ríos, Chem. Asian J. 2011, 6, 720-734
12. A. J. Metrano, S. J. Miller, J. Org. Chem. 2014, 79, 1542-1554, and references therein.
13. K. Tomohara, T. Yoshimura, R. Hyakutake, P. Yang, T. Kawabata, J. Am. Chem. Soc. 2013, 135, 13294-13297. For a recent Pd-catalyzed asymmetric synthesis of α-allyl α-alkyl piperazine-2-ones, see
14. K. M. Korch, C. Eidamshaus, D. C. Behenna, S. Nam, D. Horne, B. M. Stoltz, Angew. Chem. Int. Ed. 2015, 54, 179-183
15. Angew. Chem. 2015, 127, 181-185.
16. Synthetic preparation of N-methyl α-amino acids:, L. Aurelio, R. T. C. Brownlee, A. B. Hughes, Chem. Rev. 2004, 104, 5823-5846.
17. L. Aurelio, A. B. Hughes, in Amino Acids, Peptides and Proteins in Organic Chemistry, Vols. 1&2 (Ed.:, A. B. Hughes,), Wiley-VCH, Weinheim, 2009, pp. 245-290.
18. T. Kawakami, T. Sasaki, P. C. Reid, H. Murakami, Chem. Sci. 2014, 5, 887-893, and references therein.
19. J. Alemán, A. Milelli, S. Cabrera, E. Reyes, K. A. Jørgensen, Chem. Eur. J. 2008, 14, 10958-10966
20. H. Jiang, M. W. Paixão, D. Monge, K. A. Jørgensen, J. Am. Chem. Soc. 2010, 132, 2775-2783
21. A. N. Balaguer, X. Companyo, T. Calvet, M. Font-Bardia, A. Moyano, R. Rios, Eur. J. Org. Chem. 2009, 199-203.
22. J. L. Vicario, D. Badía, L. Carrillo, E. Reyes, Organocatalytic Enantioselective Conjugate Addition Reactions, RSC Publishing, Cambridge, 2010
23. S. B. Tsogoeva, Eur. J. Org. Chem. 2007, 1701-1716
24. D. Almasi, D. A. Alonso, C. Nájera, Tetrahedron: Asymmetry 2007, 18, 299-365.
25. O. M. Berner, L. Tedeschi, D. Enders, Eur. J. Org. Chem. 2002, 1877-1894
26. D. Roca-Lõpez, D. Sádaba, I. Delso, R. P. Herrera, T. Tejero, P. Merino, Tetrahedron: Asymmetry 2010, 21, 2562-2601
27. L. S. Aitken, N. R. Arezki, A. Dell'Isola, A. J. A. Cobb, Synthesis 2013, 2627-2628.
28. J. P. Malerich, K. Hagihara, V. R. Rawal, J. Am. Chem. Soc. 2008, 130, 14416-14417
29. Y. Zhu, J. P. Malerich, V. R. Rawal, Angew. Chem. Int. Ed. 2010, 49, 153-156
30. Angew. Chem. 2010, 122, 157-160. For reviews on squaramide catalysis, see
31. R. I. Storer, C. Aciro, L. H. Jones, Chem. Soc. Rev. 2011, 40, 2330-2346
32. J. Alemán, A. Parra, H. Jiang, K. A. Jørgensen, Chem. Eur. J. 2011, 17, 6890-6899.
33. Science of Synthesis (Ed.:, K. Maruoka,), Thieme, Stuttgart, 2012.
34. K. Hu, A. Lu, Y. Wang, Z. Zhou, C. Tang, Tetrahedron: Asymmetry 2013, 24, 953-957.
35. D. Seebach, A. R. Sting, M. Hoffmann, Angew. Chem. Int. Ed. Engl. 1996, 35, 2708-2748
36. Angew. Chem. 1996, 108, 2881-2921.
37. M. I. Calaza, C. Cativiela, Eur. J. Org. Chem. 2008, 3427-3448.
38. E. Badiola, B. Fiser, E. Gõmez-Bengoa, A. Mielgo, I. Olaizola, I. Urruzuno, J. M. García, J. M. Odriozola, J. Razkin, M. Oiarbide, C. Palomo, J. Am. Chem. Soc. 2014, 136, 17869-17881.
39. W. Yang, D.-M. Du, Org. Lett. 2010, 12, 5450-5453.
40. see:, T. J. Auvil, A. G. Schafer, A. E. Mattson, Eur. J. Org. Chem. 2014, 2633-2646.
41. N. Arshad, J. Hashim, C. O. Kappe, J. Org. Chem. 2009, 74, 5118-5121
42. S. Bepary, I. K. Youn, H.-J. Lim, G. H. Lee, Eur. J. Org. Chem. 2012, 2542-2548
43. L. Konnert, B. Reneaud, R. Marcia de Figueiredo, J.-M. Campagne, F. Lamaty, J. Martinez, E. Colacino, J. Org. Chem. 2014, 79, 10132-10142.
44. M. Meusel, M. Gütschow, Org. Prep. Proc. Int. 2004, 36, 391-443.
45. www.ccdc.cam.ac.uk/data-request/cif.
46. B. Kõtai, G. Kardos, A. Hamza, V. Farkas, I. Pápai, T. Soõs, Chem. Eur. J. 2014, 20, 5631-5639;
47. W. Y. Siau, J. Wang, Catal. Sci. Technol. 2011, 1, 1298-1310.
48. B. Tan, Y. Lu, X. Zeng, P. J. Chua, G. Zhong, Org. Lett. 2010, 12, 2682-2685
49. K. M. Lippert, K. Hof, D. Gerbig, D. Ley, H. Hausmann, S. Guenther, P. R. Schreiner, Eur. J. Org. Chem. 2012, 5919-5927
50. D. Bastida, Y. Liu, X. Tian, E. Escudero-Adán, P. Melchiorre, Org. Lett. 2013, 15, 220-223.