A tetradentate ligand for the enantioselective Ti(IV)-promoted oxidation of sulfides to sulfoxides: Origin of enantioselectivity

Journal of the American Chemical Society

Volumn 134, Issue 42, 2012, Pages 17354-17357

  Newhouse, Timothy R ^a   Li, Xin ^a   Blewett, Megan M ^a   Whitehead, Clare M C ^a   Corey, E J ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYZED OXIDATION; ENANTIOSELECTIVE; HIGH SELECTIVITY; TETRADENTATE LIGANDS;

LIGANDS; OXIDATION;

ENANTIOSELECTIVITY;

LIGAND; SULFIDE; SULFOXIDE; TETRADENTATE LIGAND; TITANIUM; UNCLASSIFIED DRUG;

ARTICLE; ENANTIOSELECTIVITY; OXIDATION;

CATALYSIS; LIGANDS; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; QUANTUM THEORY; STEREOISOMERISM; SULFIDES; SULFOXIDES; TITANIUM;

EID: 84867818358     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja305991k     Document Type: Article

References (26)

1. OMahony, G. E.; Kelly, P.; Lawrence, S. E.; Maguire, A. R. ARKIVOC 2011, I) 1
2. Wojaczynska, E.; Wojaczynski, E. Chem. Rev. 2010, 110, 4303
3. Kagan, H. B. In Organosulfur Chemistry in Asymmetric Synthesis; Taru, T.; Bolm, C., Eds.; Wiley-VCH: Weinheim, Germany, 2008.
4. Pitchen, P.; Kagan, H. B. Tetrahedron Lett. 1984, 25, 1049
5. Pitchen, P.; Duach, E.; Deshmukh, M. N.; Kagan, H. B. J. Am. Chem. Soc. 1984, 106, 8188
6. Kagan, H. B.; Duach, E.; Nemecek, C.; Pitchen, P.; Samuel, O.; Zhao, S.-H. Pure Appl. Chem. 1985, 57, 1911
7. Puchot, C.; Samuel, O.; Duach, E.; Zhao, S.; Agami, C.; Kagan, H. B. J. Am. Chem. Soc. 1986, 108, 2353
8. Zhao, S. H.; Samuel, O.; Kagan, H. B. Tetrahedron 1987, 43, 5135
9. Zhao, S. H.; Samuel, O.; Kagan, H. B. Org. Synth. 1989, 68, 49
10. Brunel, J.-M.; Diter, P.; Duetsch, M.; Kagan, H. B. J. Org. Chem. 1995, 60, 8086
11. Brunel, J. M.; Kagan, H. B. Synlett 1996, 404
12. Di Furia, F.; Modena, G.; Seraglia, R. Synthesis 1984, 325
13. Potvin, P. G.; Fieldhouse, B. G. Tetrahedron: Asymmetry 1999, 10, 1661
14. Boche, G.; Moebus, K.; Harms, K.; Marsch, M. J. Am. Chem. Soc. 1996, 118, 2770
15. Mimoun, H.; Chaumette, P.; Mignard, M.; Saussine, L.; Fischer, J.; Weiss, R. Nouv. J. Chim. 1983, 7, 467
16. Boche, G.; Moebus, K.; Harms, K.; Lohrenz, J. C. W.; Marsch, M. Chem.-Eur. J. 1996, 2, 604
17. Seenivasaperumal, M.; Federsel, H.-J.; Szabó, K. J. Adv. Synth. Catal. 2009, 351, 903
18. For stereochemical nomenclature, see: Moss, E. P. Pure Appl. Chem. 1996, 68, 2193
19. For the original nomenclature of helical handedness (lel, ob), see: Corey, E. J.; Bailar, J. C. J. Am. Chem. Soc. 1959, 81, 2620
20. All DFT calculations were performed with Gaussian 09. See: Frisch, M. J. Gaussian 09, revision A.02; Gaussian, Inc.: Wallingford, CT, 2009.
21. Structures were rendered with CYLview. See: Legault, C. Y. CYLview, version 1.0b; Université de Sherbrooke: Sherbrooke, QC, 2009; http://www.cylview.org.
22. Sharpless, K. B.; Woodward, S. S.; Finn, M. G. Pure Appl. Chem. 1983, 55, 1823
23. Corey, E. J. J. Org. Chem. 1990, 55, 1693
24. Woodward, S. S.; Finn, M. G.; Sharpless, K. B. J. Am. Chem. Soc. 1991, 113, 106
25. Finn, M. G.; Sharpless, K. B. J. Am. Chem. Soc. 1991, 113, 113
26. Cui, M.; Adam, W.; Shen, J. H.; Luo, X. M.; Tan, X. J.; Chen, K. X.; Ji, R. Y.; Jiang, H. L. J. Org. Chem. 2002, 67, 1427