Stereoarrayed CF3-Substituted 1,3-Diols by Dynamic Kinetic Resolution: Ruthenium(II)-Catalyzed Asymmetric Transfer Hydrogenation

Angewandte Chemie - International Edition

Volumn 55, Issue 17, 2016, Pages 5294-5298

  Cotman, Andrej Emanuel ^a,b   Cahard, Dominique ^c   Mohar, Barbara ^a  

^a NATIONAL INSTITUTE OF CHEMISTRY   (Slovenia)

^b UNIVERSITY OF LJUBLJANA   (Slovenia)

^c UNIVERSITÉ ET INSA DE ROUEN   (France)

Author keywords

alcohols; asymmetric catalysis; enantioselectivity; kinetic resolution; ruthenium

Indexed keywords

ALCOHOLS; CATALYSIS; ENANTIOSELECTIVITY; FORMIC ACID; HYDROGENATION; KETONES; REACTION INTERMEDIATES; RUTHENIUM;

ASYMMETRIC CATALYSIS; ASYMMETRIC TRANSFER HYDROGENATION; CYCLIC KETONES; DYNAMIC KINETIC RESOLUTION; ENANTIOPURITY; KINETIC RESOLUTION; REACTION CONDITIONS; TITLE COMPOUNDS;

KINETICS;

EID: 84961784195     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201600812     Document Type: Article

References (28)

1. V. Gouverneur, O. Lozano, Science of Synthesis, Vol.3, Georg Thieme, Stuttgart, 2011, pp. 851-930;
2. V. Bizet, T. Besset, J.-A. Ma, D. Cahard, Curr. Top. Med. Chem. 2014, 14, 901-940;
3. J. Wang, M. Sánchez-Roselló, J. L. Aceña, C. delPozo, A. E. Sorochinsky, S. Fustero, V. A. Soloshonok, H. Lu, Chem. Rev. 2014, 114, 2432-2506.
4. J. Wouters, F. Moureau, G. Evrard, J.-J. Koenig, S. Jegham, P. George, F. Durant, Bioorg. Med. Chem. 1999, 7, 1683-1693;
5. H. Shibata, H. Tsuchikawa, T. Hayashi, N. Matsumori, M. Murata, T. Usui, Chem. Asian J. 2015, 10, 915-924.
6. A. Shokri, X.-B. Wang, S. R. Kass, J. Am. Chem. Soc. 2013, 135, 9525-9530;
7. M. Samet, S. R. Kass, J. Org. Chem. 2015, 80, 7727-7731.
8. J. T. Lin, T. Yamazaki, T. Kitazume, J. Org. Chem. 1987, 52, 3211-3217;
9. S. Jeulin, S. DupratdePaule, V. Ratovelomanana-Vidal, J.-P. Genêt, N. Champion, P. Dellis, Angew. Chem. Int. Ed. 2004, 43, 320-325;
10. Angew. Chem. 2004, 116, 324-329;
11. K. Shibatomi, A. Narayama, Y. Abe, S. Iwasa, Chem. Commun. 2012, 48, 7380-7382;
12. K. Funabiki, Y. Furuno, Y. Yano, Y. Saikada, Y. Kubota, M. Matsui, Chem. Asian J. 2015, 10, 2701-2707.
13. D. Šterk, M. Stephan, B. Mohar, Org. Lett. 2006, 8, 5935-5938;
14. B. Mohar, M. Stephan, U. Urleb, Tetrahedron 2010, 66, 4144-4149.
15. A. KišiÄ?, M. Stephan, B. Mohar, Org. Lett. 2013, 15, 1614-1617;
16. A. KišiÄ?, M. Stephan, B. Mohar, Adv. Synth. Catal. 2014, 356, 3193-3198;
17. II complexes, see:
18. J. Hannedouche, G. J. Clarkson, M. Wills, J. Am. Chem. Soc. 2004, 126, 986-987;
19. A. M. Hayes, D. J. Morris, G. J. Clarkson, M. Wills, J. Am. Chem. Soc. 2005, 127, 7318-7319.
20. Crystallization medium was adopted from:, A. Ishii, M. Kanai, K. Higashiyama, K. Mikami, Chirality 2002, 14, 709-712.
21. H.-Y. Xiong, Z.-Y. Yang, Z. Chen, J.-L. Zeng, J. Nie, J.-A. Ma, Chem. Eur. J. 2014, 20, 8325-8329.
22. P. A. Dub, T. Ikariya, J. Am. Chem. Soc. 2013, 135, 2604-2619;
23. A. Matsuoka, C. A. Sandoval, M. Uchiyama, R. Noyori, H. Naka, Chem. Asian J. 2015, 10, 112-115.
24. H. Pellissier, Tetrahedron 2011, 67, 3769-3802. For selected recent examples, see:
25. S.-M. Son, H.-K. Lee, J. Org. Chem. 2014, 79, 2666-2681;
26. F. Xu, M. J. Zacuto, Y. Kohmura, J. Rosen, A. Gibb, M. Alam, J. Scott, D. Tschaen, Org. Lett. 2014, 16, 5422-5425;
27. P.-G. Echeverria, J. Cornil, C. Férard, A. Guérinot, J. Cossy, P. Phansavath, V. Ratovelomanana-Vidal, RSC Adv. 2015, 5, 56815-56819;
28. T. Cheng, Q. Ye, Q. Zhao, G. Liu, Org. Lett. 2015, 17, 4972-4975.