An organocatalyst bearing stereogenic carbon and sulfur centers as an efficient promoter for enantioselective hydrosilylation of 1,4-benzooxazines

Journal of Organic Chemistry

Volumn 78, Issue 12, 2013, Pages 6276-6280

  Liu, Xiang Wei ^a   Wang, Chao ^a   Yan, Yan ^a   Wang, Yong Qiang ^a   Sun, Jian ^a  

^a CHENGDU INSTITUTE OF BIOLOGY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALTERNATIVE APPROACH; ENANTIOSELECTIVE; HIGH YIELD; LEWIS BASE; ORGANOCATALYSTS; STEREOGENIC CARBONS;

AMINO ACIDS; CARBON; ENANTIOSELECTIVITY; HYDROSILYLATION; SULFUR;

CATALYSTS;

CARBON; LEWIS BASE; OXAZINE DERIVATIVE; PHENYLALANINE; SULFUR;

ARTICLE; CATALYST; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOSELECTIVITY; HYDROSILYLATION; SYNTHESIS;

BENZOXAZINES; CARBON; CATALYSIS; LEWIS BASES; PHENYLALANINE; SILANES; STEREOISOMERISM; SULFUR;

EID: 84879366887     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo400187e     Document Type: Article

References (45)

1. Brown, K. S.; Djerassi, C. J. Am. Chem. Soc. 1964, 86, 2451
2. Morrissey, I.; Hoshino, K.; Sato, K.; Yoshida, A.; Hayakawa, I.; Bures, M. G.; Shen, L. L. Antimicrob. Agents Chemother. 1996, 40, 1775
3. Nelson, J. M.; Chiller, T. M.; Powers, J. H.; Angulo, F. J. Clin. Infect. Dis. 2007, 44, 977
4. Miyadera, A.; Imura, A. Tetrahedron: Asymmetry 1999, 10, 119
5. Charushin, V. N.; Krasnov, V. P.; Levit, G. L.; Korolyova, M. A.; Kodess, M. I.; Chupakhin, O. N.; Kim, M. H.; Lee, H. S.; Park, Y. J.; Kim, K.-C. Tetrahedron: Asymmetry 1999, 10, 2691
6. Krasnov, V. P.; Levit, G. L.; Bukrina, I. M.; Andreeva, I. N.; Sadretdinova, L. S.; Korolyova, M. A.; Kodess, M. I.; Charushin, V. N.; Chupakhin, O. N. Tetrahedron: Asymmetry 2003, 14, 1985
7. Krasnov, V. P.; Levit, G. L.; Kodess, M. I.; Charushin, V. N.; Chupakhin, O. N. Tetrahedron: Asymmetry 2004, 15, 859
8. Potemkin, V. A.; Krasnov, V. P.; Levit, G. L.; Bartashevich, E. V.; Andreeva, I. N.; Kuzminsky, M. B.; Anikin, N. A.; Charushin, V. N.; Chupakhin, O. N. Mendeleev Commun. 2004, 14, 69
9. Atarashi, S.; Tsurumi, H.; Fujiwara, T.; Hayakawa, I. J. Heterocycl. Chem. 1991, 28, 329
10. Kang, S. B.; Ahn, E. J.; Kim, Y.; Kim, Y. H. Tetrahedron Lett. 1996, 37, 9317
11. Adrio, J.; Carretero, J. C.; Ruano, J. L. G.; Pallarés, A.; Vicioso, M. Heterocycles 1999, 51, 1563
12. Atarashi, S.; Yokohama, S.; Yamazaki, K.-I.; Sakano, K.-I.; Imamura, M.; Hayakawa, I. Chem. Pharm. Bull. 1987, 35, 1896
13. Satoh, K.; Inenaga, M.; Kanai, K. Tetrahedron: Asymmetry 1998, 9, 2657
14. Zhou, Y.-G.; Yang, P.-Y.; Han, X.-W. J. Org. Chem. 2005, 70, 1679
15. Chen, Q.-A.; Gao, K.; Duan, Y.; Ye, Z.-S.; Shi, L.; Yang, Y.; Zhou, Y.-G. J. Am. Chem. Soc. 2012, 134, 2442
16. Gao, K.; Yu, C.-B.; Wang, D.-S.; Zhou, Y.-G. Adv. Synth. Catal. 2012, 354, 483
17. Rueping, M.; Antonchick, A. P.; Theissmann, T. Angew. Chem., Int. Ed. 2006, 45, 6751
18. Rueping, M.; Sugiono, E.; Steck, A.; Theissmann, T. Adv. Synth. Catal. 2010, 352, 281
19. Bleschke, C.; Schmidt, J.; Kundu, D. S.; Blechert, S.; Thomas, A. Adv. Synth. Catal. 2011, 353, 3101
20. Jiang, Y.; Liu, L.-X.; Yuan, W.-C.; Zhang, X.-M. Synlett 2012, 23, 1797
21. Malkov, A. V.; Vranková, K.; Stoncius, S.; Kocovský, P. J. Org. Chem. 2009, 74, 5839
22. Pei, D.; Wang, Z.; Wei, S.; Zhang, Y.; Sun, J. Org. Lett. 2006, 8, 5913
23. Wang, Z.; Cheng, M.; Wu, P.; Wei, S.; Sun, J. Org. Lett. 2006, 8, 3045
24. Wang, Z.; Ye, X.; Wei, S.; Wu, P.; Zhang, A.; Sun, J. Org. Lett. 2006, 8, 999
25. Wang, Z.; Wei, S.; Wang, C.; Sun, J. Tetrahedron: Asymmetry 2007, 18, 705
26. Zhou, L.; Wang, Z.; Wei, S.; Sun, J. Chem. Commun. 2007, 2977
27. Pei, D.; Zhang, Y.; Wei, S.; Wang, M.; Sun, J. Adv. Synth. Catal. 2008, 350, 619
28. Wang, C.; Wu, X.; Zhou, L.; Sun, J. Chem. Eur. J. 2008, 14, 8789
29. Wu, X.; Li, Y.; Wang, C.; Zhou, L.; Lu, X.; Sun, J. Chem. Eur. J. 2011, 17, 2846
30. Xiao, Y.-C.; Wang, C.; Yao, Y.; Sun, J.; Chen, Y.-C. Angew. Chem., Int. Ed. 2011, 50, 10661
31. Liu, X.-W.; Yan, Y.; Wang, Y.-Q.; Wang, C.; Sun, J. Chem. Eur. J. 2012, 18, 9204
32. Guizzetti, S.; Benaglia, M. Eur. J. Org. Chem. 2010, 2010, 5529
33. Jones, S.; Warner, C. J. A. Org. Biomol. Chem. 2012, 10, 2189
34. Iwasaki, F.; Onomura, O.; Mishima, K.; Kanematsu, T.; Maki, T.; Matsumura, Y. Tetrahedron Lett. 2001, 42, 2525
35. Malkov, A. V.; Mariani, A.; MacDougall, K. N.; Kočovský, P. Org. Lett. 2004, 6, 2253
36. Malkov, A. V.; Liddon, A.; Ramirez-Lopez, P.; Bendova, L.; Haigh, D.; Kočovský, P. Angew. Chem., Int. Ed. 2006, 45, 1432
37. Zheng, H.; Deng, J.; Lin, W.; Zhang, X. Tetrahedron Lett. 2007, 48, 7934
38. Baudequin, C.; Chaturvedi, D.; Tsogoeva, S. B. Eur. J. Org. Chem. 2007, 2623
39. Guizzetti, S.; Benaglia, M.; Rossi, S. Org. Lett. 2009, 11, 2928
40. Gautier, F.-M.; Jones, S.; Martin, S. J. Org. Biomol. Chem. 2009, 7, 229
41. Kanemitsu, T.; Umehara, A.; Haneji, R.; Nagata, K.; Itoh, T. Tetrahedron 2012, 68, 3893
42. Matsumura, Y.; Ogura, K.; Kouchi, Y.; Iwasaki, F.; Onomura, O. Org. Lett. 2006, 8, 3789
43. Bonsignore, M.; Benaglia, M.; Annunziata, R.; Celentano, G. Synlett 2011, 1085
44. Zheng, Y.; Xue, Z.; Liu, L.; Shu, C.; Yuan, W.; Zhang, X. Org. Biomol. Chem. 2013, 11, 412
45. Sabitha, M. G.; Rao, A. V. S. Synth. Commun. 1987, 17, 341