Construction of tertiary alcohols bearing perfluoroalkyl chains catalyzed by prolinamide-thioureas

Journal of Organic Chemistry

Volumn 77, Issue 2, 2012, Pages 1131-1135

  Kokotos, Christoforos G ^a  

^a UNIVERSITY OF ATHENS   (Greece)

Author keywords

[No Author keywords available]

Indexed keywords

ALDOL REACTIONS; ASPARTATES; CATALYST LOADINGS; EFFICIENT CATALYSTS; HIGH ENANTIOSELECTIVITY; ORGANOCATALYSTS; PERFLUOROALKYL CHAINS; QUANTITATIVE YIELDS; SYSTEMATIC STUDY; TERTIARY ALCOHOLS;

ACETONE; CATALYSTS; CONDENSATION REACTIONS; ORGANIC COMPOUNDS;

THIOUREAS;

(1S) DITERT BUTYLASPARTATE; (1S,2S) DIPHENYLETHYLENEDIAMINE; (R) 4 HYDROXY 8 PHENYL 4 (TRIFLUOROMETHYL)OCTAN 2 ONE; (S) 2,2,2 TRIFLUORO 1 (PERFLUOROPHENYL)ETHANONE; (S) 5 CHLORO 5,5 DIFLUORO 4 HYDROXY 4 PHENYLPENTAN 2 ONE; (S) 5,5,5 TRIFLUORO 4 (4 FLUOROPHENYL) 4 HYDROXYPENTAN 2 ONE; (S) 5,5,5 TRIFLUORO 4 HYDROXY 4 (4 TRIFLUOROMETHYLPHENYL)PENTAN 2 ONE; (S) 5,5,5 TRIFLUORO 4 HYDROXY 4 4 TOLYLPENTAN 2 ONE; (S) 5,5,5 TRIFLUORO 4 HYDROXY 4 PHENYLPENTAN 2 ONE; (S) 5,5,6,6,6 PENTAFLUORO 4 HYDROXY 4 PHENYLHEXAN 2 ONE; (S) 5,5,6,6,7,7,7 HEPTAFLUORO 4 HYDROXY 4 PHENYLHEPTAN 2 ONE; (S) 5,5,6,6,7,7,8,8,8 NONAFLUORO 4 HYDROXY 4 PHENYLOCTAN 2 ONE; (S) 6,6,6 TRIFLUORO 5 HYDROXY 5 PHENYLHEXAN 3 ONE; (S) DI TERT BUTYL 2 [3 [(1S,2S) 1,2 DIPHENYL 2 [(S) (PYRROLIDINE 2 CARBOXAMIDO] ETHYL]THIOUREIDO]SUCCINATE; (S) ETHYL 3 HYDROXY 5 OXO 3 (TRIFLUOROMETHYL)HEXANOATE; (S) PROLINAMIDE; 2,2,2 TRIFLUOROMETHYL 1 PHENYLETHANONE; 3,4 DIHYDROXY 8 PHENYL 4 (TRIFLUOROMETHYL)OCTAN 2 ONE; ACETONE; ALCOHOL DERIVATIVE; KETONE; ORGANIC COMPOUND; THIOUREA DERIVATIVE; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; CATALYST; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; QUANTITATIVE ANALYSIS; SYNTHESIS;

EID: 84856085861     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo2020104     Document Type: Article

References (49)

1. List, B.; Lerner, R. A.; Barbas, C. F., III J. Am. Chem. Soc. 2000, 122, 2395-2396
2. Ahrendt, K. A.; Borths, C. J.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 4243-4244
3. For a book, see: In Enantioselective Organocatalysis: Reactions and Experimental Procedures; Dalko, P. I., Ed.; Wiley-VCH: Weinheim, Germany, 2007.
4. Zhong, C.; Shi, X. Eur. J. Org. Chem. 2010, 2999-3025
5. Brazier, B.; Tomkinson, N. C. O. Top. Curr. Chem. 2010, 291, 281-347
6. For a recent review on aldol reaction, see: Trost, B. M.; Brindle, C. S. Chem. Soc. Rev. 2010, 39, 1600-1632
7. Guillena, G.; Najera, C.; Ramon, D. J. Tetrahedron: Asymmetry 2007, 18, 2249-2293
8. Adachi, S.; Herada, T. Eur. J. Org. Chem. 2009, 3661-3671
9. Chen, W.-B.; Du, X.-L.; Cun, L.-F.; Zhang, X.-M.; Yuan, W.-C. Tetrahedron 2010, 66, 1441-1446
10. Qiu, L.-H.; Shen, Z.-X.; Shi, C.-Q.; Liu, Y.-H.; Zhang, Y.-W. Chin. J. Chem. 2005, 23, 584-588
11. Hiyama, T. In Organofluorine Compounds: Chemistry and Applications; Springer: New York, 2000.
12. In Bioorganic and Medicinal Chemistry of Fluorine; Begue, J.-P.; Bonnet-Delpon, D., Eds.; Wiley-VCH: Hoboken, NJ, 2008.
13. Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320-330
14. Eignerova, B.; Dracinsky, M.; Kotora, M. Eur. J. Org. Chem. 2008, 4493-4499
15. Barata-Vallejo, S.; Postigo, A. J. Org. Chem. 2010, 75, 6141-6148
16. Wang, X.-J.; Zhao, Y.; Liu, J.-T. Org. Lett. 2007, 9, 1343-1345
17. Zhang, D.; Yuan, C. Tetrahedron 2008, 64, 2480-2488
18. For a book, see: In Quaternary Stereocenters: Challenges and Solutions for Organic Synthesis; Christoffers, J.; Baro, A., Eds.; Wiley-VCH: Weinheim, Germany, 2005.
19. Riant, O.; Hannedouche, J. Org. Biomol. Chem. 2007, 5, 873-888
20. Corey, E. J.; Guzman-Perez, A. Angew. Chem., Int. Ed. 1998, 37, 388-401
21. Shibasaki, M.; Kanai, M. Chem. Rev. 2008, 108, 2853-2873
22. Stymiest, J. L.; Bagutski, V.; French, R. M.; Aggarwal, V. K. Nature 2008, 456, 778-782
23. Prakash, G. K. S.; Yudin, A. K. Chem. Rev. 1997, 97, 757-786
24. Prakash, G. K. S.; Panja, C.; Vaghoo, H.; Surampudi, V.; Kultyshev, R.; Mandal, M.; Rasul, G.; Mathew, T.; Olah, G. A. J. Org. Chem. 2006, 71, 6806-6813
25. Bastos, R. S. Synlett 2008, 1425-1426
26. Dilman, A. D.; Levin, V. V. Eur. J. Org. Chem. 2011, 831-841
27. Song, J. J.; Xu, J.; Tan, Z.; Reeves, J. T.; Grinberg, N.; Lee, H.; Kuzmich, K.; Feng, X.; Yee, N. K.; Senanayake, C. H. Org. Process Res. Dev. 2007, 11, 534-538
28. Sebhat, I. K.; Franklin, C.; Lo, M. M.-C.; Chen, D.; Jewell, J. P.; Miller, R.; Pang, J.; Palyha, O.; Kan, Y.; Kelly, T. M.; Guan, X.-M.; Marsh, D. J.; Kosinski, J. A.; Metzger, J. M.; Lyons, K.; Dragovic, J.; Guzzo, P. R.; Henderson, A. J.; Reitman, M. L.; Narund, R. P.; Wyvratt, M. J.; Lin, L. S. ACS Med. Chem. Lett. 2011, 2, 43-47
29. Hara, N.; Tamura, R.; Funahashi, Y.; Nakamura, S. Org. Lett. 2011, 13, 1662-1665
30. Bellis, E.; Vasilatou, K.; Kokotos, G. Synthesis 2005, 2407-2413
31. Cobb, A. J. A.; Shaw, D. M.; Longbottom, D. A.; Gold, J. B.; Ley, S. V. Org. Biomol. Chem. 2005, 3, 84-96
32. Mase, N.; Tanaka, F.; Barbas, C. F., III Org. Lett. 2003, 5, 4369-4372
33. Mase, N.; Tanaka, F.; Barbas, C. F., III Angew. Chem., Int. Ed. 2004, 43, 2420-2423
34. For a review, see: Mielgo, A.; Palomo, C. Chem.-Asian J. 2008, 3, 922-948
35. For a review, see: Lelais, G.; MacMillan, D. W. C. Aldrichimica Acta 2006, 39, 79-87
36. Tsandi, E.; Kokotos, C. G.; Kousidou, S.; Ragoussis, V.; Kokotos, G. Tetrahedron 2009, 65, 1444-1449
37. Kokotos, C. G.; Kokotos, G. Adv. Synth. Catal. 2009, 351, 1355-1362
38. Fotaras, S.; Kokotos, C. G.; Tsandi, E.; Kokotos, G. Eur. J. Org. Chem. 2011, 1310-1317
39. Kokotos, C. G.; Limnios, D.; Triggidou, D.; Trifonidou, M.; Kokotos, G. Org. Biomol. Chem. 2011, 9, 3386-3395
40. For a review, see: Liu, X.; Lin, L.; Feng, X. Chem. Commun. 2009, 6145-6158
41. Tang, Z.; Yang, Z. H.; Chen, X. H.; Cun, L. F.; Mi, A. Q.; Jiang, Y. Z.; Gong, L. Z. J. Am. Chem. Soc. 2005, 127, 9285-9289
42. Samanta, S.; Liu, J.; Dodda, R.; Zhao, C.-G. Org. Lett. 2005, 7, 5321-5323
43. Vishnumaya, M. Raj; Ginotra, S. K.; Singh, V. K. Org. Lett. 2006, 8, 4097-4099
44. Wang, B.; Chen, G.-H.; Liu, L.-Y.; Chang, W.-X.; Li, J. Adv. Synth. Catal. 2009, 351, 2441-2448
45. Fotaras, S.; Kokotos, C. G.; Kokotos, G. manuscript submitted.
46. Lopez-Vales, R.; Navarro, X.; Shimizu, T.; Baskakis, C.; Kokotos, G.; Constantinou-Kokotou, V.; Stephens, D.; Dennis, E. A.; David, S. Brain 2008, 131, 2620-2631
47. Kalyvas, A.; Baskakis, C.; Magrioti, V.; Constantinou-Kokotou, V.; Stephens, D.; Dennis, E. A.; Kokotos, G.; David, S. Brain 2009, 132, 1221-1235
48. Kokotos, G.; Hsu, Y.-H.; Burke, J. E.; Baskakis, C.; Kokotos, C. G.; Magrioti, V.; Dennis, E. A. J. Med. Chem. 2010, 53, 3602-3610
49. Kokotos, C. G.; Baskakis, C.; Kokotos, G. J. Org. Chem. 2008, 73, 8623-8626