Asymmetric epoxidation catalyzed by α,α-dimethylmorpholinone ketone. Methyl group effect on spiro and planar transition states

Journal of Organic Chemistry

Volumn 74, Issue 16, 2009, Pages 6335-6338

  Wong, O Andrea ^a   Wang, Bin ^a   Zhao, Mei Xin ^a   Shi, Yian ^a  

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

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CATALYSTS; OLEFINS;

ASYMMETRIC EPOXIDATION; CHEMICAL EQUATIONS; COMBINED FEATURES; DIMETHYL GROUPS; METHYL GROUP; PLANAR TRANSITION STATE; SIGNIFICANT IMPACTS;

KETONES;

ALKENE; ALPHA,ALPHA DIMETHYLMORPHOLINONE KETONE; KETONE DERIVATIVE; UNCLASSIFIED DRUG; EPOXIDE; KETONE; MORPHOLINE DERIVATIVE; SPIRO COMPOUND;

ARTICLE; CATALYSIS; CATALYST; CHIRALITY; EPOXIDATION; CHEMISTRY;

ALKENES; CATALYSIS; EPOXY COMPOUNDS; KETONES; MORPHOLINES; SPIRO COMPOUNDS;

EID: 70349159538     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo900739q     Document Type: Article

References (26)

1. For leading reviews, see: (a) Denmark, S. E.; Wu, Z. Synlett 1999, 847.
2. (b) Frohn, M.; Shi, Y. Synthesis 2000, 1979.
3. (c) Shi, Y. Acc. Chem. Res. 2004, 37, 488.
4. (d) Yang, D. Acc. Chem. Res. 2004, 37, 497.
5. (e) Wong, O. A.; Shi, Y. Chem. Rev. 2008, 108, 3958.
6. (a) Tu, Y.; Wang, Z.-X.; Shi, Y. J. Am. Chem. Soc. 1996, 118, 9806.
7. (b) Wang, Z.-X.; Tu, Y.; Frohn, M.; Zhang, J.-R.; Shi, Y. J. Am. Chem. Soc. 1997, 119, 11224.
8. (c) Shu, L.; Shi, Y. Tetrahedron 2001, 57, 5213.
9. (a) Tian, H.; She, X.; Shu, L.; Yu, H.; Shi, Y. J. Am. Chem. Soc. 2000, 122, 11551.
10. (b) Tian, H.; She, X.; Xu, J.; Shi, Y. Org. Lett. 2001, 3, 1929.
11. (c) Tian, H.; She, X.; Yu, H.; Shu, L.; Shi, Y. J. Org. Chem. 2002, 67, 2435.
12. (d) Shu, L.; Wang, P.; Gan, Y.; Shi, Y. Org. Lett. 2003, 5, 293.
13. (e) Shu, L.; Shi, Y. Tetrahedron Lett. 2004, 45, 8115.
14. (f) Goeddel, D.; Shu, L.; Yuan, Y.; Wong, O. A.; Wang, B.; Shi, Y. J. Org. Chem. 2006, 71, 1715.
15. (g) Wong, O. A.; Shi, Y. J. Org. Chem. 2006, 71, 3973.
16. (h) Shen, Y.-M.; Wang, B.; Shi, Y. Angew. Chem., Int. Ed. 2006, 45, 1429.
17. (i) Shen, Y.-M.; Wang, B.; Shi, Y. Tetrahedron Lett. 2006, 47, 5455.
18. (j) Wang, B.; Shen, Y.-M.; Shi, Y. J. Org. Chem. 2006, 71, 9519.
19. (k) Burke, C. P.; Shi, Y. Angew. Chem., Int. Ed. 2006, 45, 4475.
20. (l) Burke, C. P.; Shi, Y. J. Org. Chem. 2007, 72, 4093.
21. (m) Burke, C. P.; Shi, Y. J. Org. Chem. 2007, 72, 6320.
22. Wang, B.; Wong, O. A.; Zhao, M.-X.; Shi, Y. J. Org. Chem. 2008, 73, 9539.
23. Crane, Z.; Goeddel, D.; Gan, Y.; Shi, Y. Tetrahedron 2005, 61, 6409.
24. 3-AcOH, pH 9.3) (5.0 mL) at 0 °C for 3.5 h].
25. Zhao, M.-X.; Goeddel, D.; Li, K.; Shi, Y. Tetrahedron 2006, 62, 8064.
26. Zhu, Y.; Shu, L.; Tu, Y.; Shi, Y. J. Org. Chem. 2001, 66, 1818.