Activation of 1,2- and 1,3-ketoamides with thiourea organocatalyst for the enantioselective domino synthesis of functionalized cyclohexanes

Synthesis (Germany)

Volumn 45, Issue 12, 2013, Pages 1659-1666

  Raimondi, Wilfried ^a   Sanchez Duque, Mariadel Mar ^a   Goudedranche, Sébastien ^a   Quintard, Adrien ^a   Constantieux, Thierry ^a   Bugaut, Xavier ^a   Bonne, Damien ^a   Rodriguez, Jean ^a  

^a AIX MARSEILLE UNIVERSITÉ   (France)

Author keywords

amides; catalysis; cyclizations; cycloalkanes; domino reactions; ketones; stereoselectivity; thioureas

Indexed keywords

CYCLIZATIONS; CYCLO-ALKANES; DOMINO REACTIONS; EFFICIENT CONTROL; ENANTIOSELECTIVE; FUNCTIONALIZED; ORGANOCATALYSTS; STEREOGENIC CENTERS;

AMIDES; CATALYSIS; CATALYSTS; CYCLOHEXANE; KETONES; ORGANIC COMPOUNDS; REACTION KINETICS; STEREOSELECTIVITY;

THIOUREAS;

1,2 KETOAMIDE; 1,3 KETOAMIDE; 2 ETHYL 1 HYDROXY N (4 METHOXYPHENYL) 4,6 DINITRO 3,5 DIPHENYLCYCLOHEXANECARBOXAMIDE; 2 ETHYL 3,5 BIS(4 FLUOROPHENYL) 1 HYDROXY N (4 METHOXYPHENYL) 4,6 DINITROCYCLOHEXANECARBOXAMIDE; 3,5 BIS (4 FLUOROPHENYL) 1 HYDROXY 2 METHYL 4,6 DINITRO N PHENYLCYCLOHEXANECARBOXAMIDE; 4 HYDROXY 8 OXO N PHENYLBICYCLO[3.2.1.] OCTANE 1 CARBOXAMIDE; 4 HYDROXY 8 OXO N TOSYLBICYCLO[3.2.1.] OCTANE 1 CARBOXAMIDE; 4 HYDROXY N (4 NITROPHENYL) 8 OXOBICYCLO[3.2.1.] OCTANE 1 CARBOXAMIDE; 4 HYDROXY N 1 NAPHTHYL 8 OXOBICYCLO[3.2.1.] OCTANE 1 CARBOXAMIDE; 4,8 DIOXO N TOSYLBICYCLO[3.2.1.] OCTANE 1 CARBOXAMIDE; AMIDE; CYCLOHEXANE; N (2,5 DICHLOROPHENYL) 2 ETHYL 3,5 BIS(4 FLUOROPHENYL) 1 HYDROXY 4,6 DINITROCYCLOHEXANECARBOXAMIDE; N (4 CHLOROPHENYL) 2 ETHYL 3,5 BIS(4 FLUOROPHENYL) 1 HYDROXY 4,6 DINITROCYCLOHEXANECARBOXAMIDE; THIOUREA; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; CHEMICAL STRUCTURE; CHIRALITY; COLUMN CHROMATOGRAPHY; CYCLIZATION; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

EID: 84878775670     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0033-1338844     Document Type: Article

References (30)

1. Enders D., Grondal C., Hüttl M. R. M. Angew. Chem. Int. Ed.: 2007; 46 1570
2. Yu X., Wang W. Org. Biomol. Chem.: 2008; 6 2037
3. Alba A.-N, Companyo X., Viciano M., Rios R. Curr. Org. Chem.: 2009; 13 1432
4. Grondal C., Jeanty M., Enders D. Nature Chem.: 2010; 2 167
5. Pellisier H. Adv. Synth. Catal.: 2012; 354 237
6. Halland N., Aburel P. S., Jorgensen K. A. Angew. Chem. Int. Ed.: 2004; 43 1272
7. Zhou J., List B. J. Am. Chem. Soc.: 2007; 129 7498
8. Reyes E., Jiang H., Milelli A., Elsner P., Hazell R. G., Jorgensen K. A. Angew. Chem. Int. Ed.: 2007; 46 902
9. McGarraugh P. G., Brenner S. E. Org. Lett.: 2009; 11 5654
10. Hayashi Y., Okano T., Aratake S., Hazelard D. Angew. Chem. Int. Ed.: 2007; 46 4922
11. Anwar S., Chang H.-J, Chen K. Org. Lett.: 2011; 13 2200
12. Ramachary D. B., Chowdari N. S., Barbas C. F. III. Angew. Chem. Int. Ed.: 2003; 42 4233
13. Enders D., Hüttl M. R. M, Runsik Y., Raabe G., Wendt B. Angew. Chem. Int. Ed.: 2007; 46 467
14. Penon O., Carlone A., Mazzanti A., Locatelli M., Sambri L., Bartoli G., Melchiorre P. Chem. Eur. J.: 2008; 14 4788
15. Wang Y., Han R. G., Zhao Y. L., Yang S., Xu P. F., Dixon D. J. Angew. Chem. Int. Ed.: 2009; 48 9834
16. Jiang K., Jia Z.-J, Yin X., Wu L., Chen Y.-C. Org. Lett.: 2010; 12 2766
17. Jia Y., Mao Z., Wang R. Tetrahedron: Asymmetry: 2011; 22 2018
18. For the concept underlying this subject, see: Bonne D., Constantieux T., Coquerel Y., Rodriguez J. Chem. Eur. J.: 2013; 19 2218
19. For a review, see: Bonne D., Constantieux T., Coquerel Y., Rodriguez J. Tetrahedron: Asymmetry: 2010; 21 1085
20. Baslé O., Raimondi W., Sanchez Duque M. M., Bonne D., Constantieux T., Rodriguez J. Org. Lett.: 2010; 12 5246
21. Sanchez Duque M. M., Baslé O., Isambert N., Gaudel-Siri A., Génisson Y., Plaquevent J.-C, Rodriguez J., Constantieux T. Org. Lett.: 2011; 13 3296
22. Nakamura A., Lectard S., Hashizume D., Hamashima Y., Sodeoka M. J. Am. Chem. Soc.: 2010; 132 4036
23. Shi D., Xie Y., Zhou H., Xia C., Huang H. Angew. Chem. Int. Ed.: 2012; 51 1248
24. Varga S., Jakab G., Drahos L., Holczbauer T., Czugler M., Soós T. Org. Lett.: 2011; 13 5416
25. Presset M., Coquerel Y., Rodriguez J. ChemCatChem: 2012; 4 172
26. Presset M., Coquerel Y., Rodriguez J. Chem. Rev.: 2013; 113 525
27. Boddaert T., Coquerel Y., Rodriguez J. Adv. Synth. Catal.: 2009; 351 1744
28. Boddaert T., Coquerel Y., Rodriguez J. Chem. Eur. J.: 2011; 17 2266
29. Raimondi W., Bonne D., Rodriguez J. Angew. Chem. Int. Ed.: 2012; 51 40
30. Raimondi W., Bonne D., Rodriguez J. Chem. Commun.: 2012; 48 6763