Asymmetric synthesis of sulfinamides using (-)-quinine as chiral auxiliary

Journal of Organic Chemistry

Volumn 77, Issue 1, 2012, Pages 690-695

  Zhang, Yongda ^a   Chitale, Sampada ^a   Goyal, Navneet ^a   Li, Guisheng ^a   Han, Zhengxu S ^a   Shen, Sherry ^a   Ma, Shengli ^a   Grinberg, Nelu ^a   Lee, Heewon ^a   Lu, Bruce Z ^a   Senanayake, Chris H ^a  

^a BOEHRINGER INGELHEIM PHARMACEUTICALS INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ASYMMETRIC SYNTHESIS; CHIRAL AUXILIARIES; GOOD YIELD; SULFINAMIDES;

CHEMISTRY;

ORGANIC COMPOUNDS;

GRIGNARD REAGENT; QUININE; SULFINAMIDE;

ARTICLE; ASYMMETRIC SYNTHESIS; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CHIRALITY; COLUMN CHROMATOGRAPHY; DIASTEREOISOMER; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; STRUCTURE ANALYSIS;

INDICATORS AND REAGENTS; MOLECULAR STRUCTURE; QUININE; STEREOISOMERISM; SULFONAMIDES; SULFONIUM COMPOUNDS;

EID: 84862952931     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo201825b     Document Type: Article

References (39)

1. Ruano, J. L. G.; Aleman, J.; Cid, M. B.; Fernandez-Ibanez, A.; Mesestro, M. C.; Martin, M. R.; Martin-Castro, A. M. In Organosulfur Chemistry in Asymmetric Synthesis; Toru, T., Bolm, C., Eds.; Wiley-VCH: Weinheim, Germany, 2008; p 55.
2. Senanayake, C. H.; Han, Z.; Krishnamurthy, D. In Organosulfur Chemistry in Asymmetric Synthesis; Toru, T., Bolm, C., Eds.; Wiley-VCH: Weinheim, Germany, 2008; p 234.
3. Senanayake, C. H.; Krishnamurthy, D.; Lu, Z.-H.; Han, Z.; Gallou, I. Aldrichimica Acta 2005, 38 (3) 93
4. Morton, D.; Stockman, R. A. Tetrahedron 2006, 62, 8869
5. Ellman, J. A.; Owens, T. D.; Tang, T. P. Acc. Chem. Res. 2002, 35, 984
6. Robak, M. T.; Herbage, M. A.; Ellman, J. A. Chem. Rev. 2010, 110, 3600
7. Zhou, P.; Chen, B.-C.; Davis, F. A. Tetrahedron 2004, 60, 8003
8. Ellman, J. A.; Kochi, T. J. Am. Chem. Soc. 2004, 126, 15652
9. Davis, F. A.; Zhang, Y. Tetrahedron Lett. 2009, 50, 5205
10. Akindele, T.; Yamamoto, Y.; Maekawa, M.; Umeki, H.; Yamada, K.-I.; Tomioka, K. Org. Lett. 2006, 8, 5729
11. Kochi, T.; Tang, T. P.; Ellman, J. A. J. Am. Chem. Soc. 2002, 124, 6518
12. Denolf, B.; Leemans, E.; Kimpe, N. D. J. Org. Chem. 2007, 72, 3211
13. Chen, Q.; Yuan, C. Synthesis 2007, 24, 3779
14. Hamzik, P, J.; Brubaker, J. D. Org. Lett. 2010, 12, 1116
15. See examples of synthesis of chiral amines by hydrogenation: Fleury-Brégeot, N.; de la Fuente, V.; Castillón, S.; Claver, C. ChemCatChem 2010, 2, 1346
16. Owens, T. D.; Frederick J. Hollander, F. J.; Oliver, A. G.; Ellma, J. A. J. Am. Chem. Soc. 2001, 123, 1539
17. Kimmel, K. L.; Robak, M. T.; Ellman, J. A. J. Am. Chem. Soc. 2009, 131, 8754
18. Robak, M. T.; Trincado, M.; Ellman, J. A. J. Am. Chem. Soc. 2007, 129, 15110
19. Xu, H.; Zuend, S. J.; Woll, M. G.; Tao, Y.; Jacobsen, E. N. Science 2010, 327, 986
20. Solà, J.; Revés, M.; Riera, A.; Verdaguer, X. Angew. Chem., Int. Ed. 2007, 46, 5020
21. Cogan, D. A.; Liu, G.; Kim, K.; Backes, B. J.; Ellman, J. A. J.Am. Chem. Soc. 1998, 120, 8011
22. Weix, D. J.; Ellman, J. A. Org. Lett. 2003, 5, 1317
23. Weix, D. J.; Ellman, J. A. Org. Synth. 2005, 82, 157
24. Enzyme-catalyzed resolution of N -acyl arylsulfinamides: Savile, C. K.; Magloire, V. P.; Kazlauskas, R. J. J. Am. Chem. Soc. 2005, 127, 2104
25. Han, Z.; Krishnamurthy, D.; Paul Grover, P.; Fang, Q. K.; Senanayake, C. H. J. Am. Chem. Soc. 2002, 124, 7880
26. Han, Z.; Meyer, A. M.; Xu, Y.; Zhang, Y.; Busch, R.; Shen, S.; Grinberg, N; Lu, B. Z.; Krishnamurthy, D.; Senanayake, C. H. J. Org. Chem. 2011, 76, 5480
27. Lu, B. Z.; Jin, F.; Zhang, Y.; Wu, X.; Wald, S. A.; Senanayake, C. H. Org. Lett. 2005, 7, 1465
28. Peltier, H. M.; Evans, J. W.; Ellman, J. A. Org. Lett. 2005, 7, 1733
29. Shibata, N.; Matsunaga, M.; Fukuzumi, T.; Nakamura, S.; Toru, T. Synlett. 2005, 11, 1699
30. Ruano, J. L. G.; Parra, A.; Yuste, F.; Mastranzo, V. M. Synthesis 2008, 2, 311
31. Achard, T.; Benet-Buchholz, J.; Riera, A.; Verdaguer, X. Organometallics 2009, 28, 480
32. Ji, Y.; Riera, A.; Verdaguer, X. Org. Lett. 2009, 11, 4346
33. Mellah, M.; Voituriez, A.; Schulz, E. Chem. Rev. 2007, 107, 5133
34. Beck, E. M.; Hyde, A. M.; Jacobsen, E, N. Org. Lett. 2011, 13, 4263
35. Brak, K.; Barrett, K. T.; Ellman, J. A. J. Org. Chem. 2009, 74, 3606
36. Brun, S.; Parera, M.; Pla-Quintana, A.; Roglans, A.; León, T.; Achard, T.; Solà, J.; Verdaguer, X.; Riera, A. Tetrahedron 2010, 66, 9032
37. Revés, M.; Achard, T.; Solà, J.; Riera, A.; Verdaguer, X. J. Org. Chem. 2008, 73, 7080
38. Kunio, H.; Takashi, W. Heterocycles 2001, 54, 73-76
39. Gölz, H.; Glatz, B.; Has, G.; Helmchen, G.; Muxfeldt, H. Angew. Chem. 1977, 89, 742