Enantioselective N-heterocyclic carbene-catalyzed β-hydroxylation of enals using nitroarenes: An atom transfer reaction that proceeds via single electron transfer

Journal of the American Chemical Society

Volumn 136, Issue 42, 2014, Pages 14674-14677

  White, Nicholas A ^a   Rovis, Tomislav ^a  

^a Department of Environmental and Radiological Health Sciences   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ATOM TRANSFER; ENANTIOSELECTIVE; N-HETEROCYCLIC CARBENES; NITROARENES; SINGLE ELECTRON TRANSFER;

CARBENE; HETEROCYCLIC COMPOUND; NITROBENZENE DERIVATIVE; OXYGEN; POLYCYCLIC AROMATIC HYDROCARBON; BENZENE; METHANE;

ARTICLE; ATOM; CATALYSIS; CATALYST; ELECTRON; ELECTRON TRANSPORT; ELECTROPHILICITY; ENANTIOMER; ENANTIOSELECTIVITY; EPOXIDATION; HYDROXYLATION; NUCLEOPHILICITY; OXIDATION; PROTON TRANSPORT; REACTION ANALYSIS; SYNTHESIS; ANALOGS AND DERIVATIVES; CHEMISTRY; ENZYME SPECIFICITY; STEREOISOMERISM;

BENZENE; CATALYSIS; ELECTRON TRANSPORT; HETEROCYCLIC COMPOUNDS; HYDROXYLATION; METHANE; STEREOISOMERISM; SUBSTRATE SPECIFICITY;

EID: 84908432158     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja5080739     Document Type: Article

References (33)

1. Moore, J. L.; Rovis, T. Top. Curr. Chem. 2010, 291, 77
2. Vora, H. U.; Rovis, T. Aldrichimica Acta 2011, 44, 1
3. Bugaut, X.; Glorius, F. Chem. Soc. Rev. 2012, 41, 3511
4. Ciganek, E. Synthesis 1995, 1311
5. Enders, D.; Breuer, K.; Runsink, J.; Teles, J. H. Helv. Chim. Acta 1996, 79, 1899
6. Kerr, M. S.; Read de Alaniz, J.; Rovis, T. J. Am. Chem. Soc. 2002, 124, 10298
7. Chow, K. Y.-K.; Bode, J. W. J. Am. Chem. Soc. 2004, 126, 8126
8. Reynolds, N. T.; Read de Alaniz, J.; Rovis, T. J. Am. Chem. Soc. 2004, 126, 9518
9. DiRocco, D. A.; Rovis, T. J. Am. Chem. Soc. 2011, 133, 10402
10. Chan, A.; Scheidt, K. A. Org. Lett. 2005, 7, 905
11. Sohn, S. S.; Bode, J. W. Org. Lett. 2005, 7, 3873
12. Burstein, C.; Glorius, F. Angew. Chem., Int. Ed. 2004, 43, 6205
13. Sohn, S. S.; Rosen, E. L.; Bode, J. W. J. Am. Chem. Soc. 2004, 126, 14370
14. He, M.; Bode, J. W. Org. Lett. 2005, 7, 3131
15. Raup, D. E. A.; Cardinal-David, B.; Holte, D.; Scheidt, K. A. Nat. Chem. 2010, 2, 766
16. Zhao, X.; DiRocco, D. A.; Rovis, T. J. Am. Chem. Soc. 2011, 133, 12466
17. Nair, V.; Sinu, C. R.; Babu, B. P.; Varghese, V.; Jose, A.; Suresh, E. Org. Lett. 2009, 11, 5570
18. Maji, B.; Ji, L.; Wang, S.; Vedachalam, S.; Rakesh, G.; Liu, X.-W. Angew. Chem., Int. Ed. 2012, 51, 8276
19. White, N. A.; DiRocco, D. A.; Rovis, T. J. Am. Chem. Soc. 2013, 135, 8504
20. Maki, B. E.; Scheidt, K. A. Org. Lett. 2008, 10, 4331
21. Guin, J.; De Sarkar, S.; Grimme, S.; Studer, A. Angew. Chem., Int. Ed. 2008, 47, 8727
22. De Sarkar, S.; Grimme, S.; Studer, A. J. Am. Chem. Soc. 2010, 132, 1190
23. For the seminal report of asymmetric organocatalysis proceeding via one-electron pathways, see: Beeson, T. D.; Mastracchio, A.; Hong, J.-B.; Ashton, K.; MacMillan, D. W. C. Science 2007, 316, 582-585
24. DiRocco, D. A.; Oberg, K. M.; Rovis, T. J. Am. Chem. Soc. 2012, 134, 6143
25. Wardman, P. J. Phys. Chem. Ref. Data 1989, 18, 1637
26. Zieba-Mizgala, A.; Puszko, A.; Regiec, A.; Kuduk-Jaworska, J. Bioelectrochemistry 2005, 65, 113
27. We had previously demonstrated the enantioselective dehydrogenative coupling of tetrahydroquinolines and aliphatic aldehydes using NHCs and photoredox catalysis. The oxidative quencher used in that chemistry was m -dinitrobenzene. See: DiRocco, D. A.; Rovis, T. J. Am. Chem. Soc. 2012, 134, 8094
28. Jiang, H.; Gschwend, B.; Albrecht,.; Jørgensen, K. A. Org. Lett. 2010, 12, 5052
29. Kaeobamrung, J.; Mahatthananchai, J.; Zheng, P.; Bode, J. W. J. Am. Chem. Soc. 2010, 132, 8810
30. Cheng, J.; Huang, Z.; Chi, Y. R. Angew. Chem., Int. Ed. 2013, 52, 8592
31. Bartoli, G.; Dalpozzo, R.; Nardi, M. Chem. Soc. Rev. 2014, 43, 4728
32. Bosco, M.; Dalpozzo, R.; Bartoli, G.; Palmieri, G.; Petrini, M. J. Chem. Soc., Perkin Trans. 2 1991, 657
33. The bond rotational barrier in the parent allyl radical has been determined to be 15.7 ± 1.0 kcal/mol. See: Korth, H.-G.; Trill, H.; Sustmann, R. J. Am. Chem. Soc. 1981, 103, 4483