Chiral sodium phosphate catalyzed enantioselective 1,4-addition of TMSCN to aromatic enones

Synlett

Volumn , Issue 18, 2010, Pages 2725-2728

  Yang, Jingya ^a,b   Wu, Shaoxiang ^a   Chen, Fu Xue ^a  

^a BEIJING INSTITUTE OF TECHNOLOGY   (China)

^b NORTHWEST NORMAL UNIVERSITY   (China)

Author keywords

1,4 addition; asymmetric catalysis; enones; nitriles; phosphates

Indexed keywords

1,1' BINAPHTHYL 2,2' DIYLPHOSPHORIC ACID; 2,2' DIHYDROXY 1,1' BINAPHTHYL; 3,3' DI(1 ADAMANTYL) 1,1' BINAPHTHYL 2,2' DIYLPHOSPHORIC ACID; 4 OXO 2,4 DIPHENYLBUTANENITRILE; AROMATIC COMPOUND; BETA CYANO KETONE; CAMPHOR SULFONIC ACID; SODIUM; SODIUM DIHYDROGEN PHOSPHATE; TARTARIC ACID; TOLUENE; TRIMETHYLSILYL CYANIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; CRYSTAL STRUCTURE; CRYSTALLIZATION; ELECTRON; ENANTIOSELECTIVITY; TEMPERATURE; X RAY CRYSTALLOGRAPHY;

EID: 78149283092     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0030-1258817     Document Type: Article

References (44)

1. Ji J.-X, Chan A S. C., In Catalytic Asymmetric Synthesis 3rd ed. Ojima I Wiley New Jersey 2010 439-495
2. Shintani R, Hayashi T, In New Frontiers in Asymmetric Catalysis Mikami K Lautens M Wiley New Jersey 2007 59-100
3. Brock S, Hose D R. J., Moseley J D., Parker A J., Patel I, Williams A J., Org. Process Res. Dev. 2008 12 496
4. Hayashi T, Yamasaki K, Chem. Rev. 2003 103 2829
5. Harutyunyan S R., Hartog T, Geurts K, Minnaard A J., Feringa B L., Chem. Rev. 2008 108 2824
6. López F, Minnaard A J., Feringa B L., Acc. Chem. Res. 2007 40 179
7. Wang J, Li W, Liu Y, Chu Y, Lin L, Liu X, Feng X, Org. Lett. 2010 12 1280
8. Mazet C, Jacobsen E N., Angew. Chem. Int. Ed. 2008 47 1762
9. Madhavan N, Weck M, Adv. Synth. Catal. 2008 350 419
10. Fujimori I, Mita T, Maki K, Shiro M, Sato A, Furusho S, Kanai M, Shibasaki M, Tetrahedron 2007 63 5820
11. Mita T, Sasaki K, Kanai M, Shibasaki M, J. Am. Chem. Soc. 2005 127 514
12. Sammis G M., Danjo H, Jacobsen E N., J. Am. Chem. Soc. 2004 126 9928
13. Sammis G M., Jacobsen E N., J. Am. Chem. Soc. 2003 125 4442
14. Tanaka Y, Kanai M, Shibasaki M, J. Am. Chem. Soc. 2008 130 6072
15. Tanaka Y, Kanai M, Shibasaki M, [nl]J. Am. Chem. Soc. 2010 132 8862
16. Shibasaki M, Kanai M, Matsunaga S, Kumagai N, Acc. Chem. Res. 2009 42 1117
17. Yang J, Wang Y, Wu S, Chen F.-X, Synlett 2009 3365
18. Yang J, Chen F.-X, Chin. J. Chem. 2010 28 981
19. Yang J, Shen Y, Chen F.-X, Synthesis 2010 1325
20. For reports using chiral alkali metal salts of amino acids, see:, Yamaguchi M, Yokota N, Minami T, J. Chem. Soc., Chem. Commun. 1991 1088
21. Yamaguchi M, Shiraishi T, Hirama M, Angew. Chem., Int. Ed. Engl. 1993 32 1176
22. Yamaguchi M, Shiraishi T, Igarashi Y, Hirama M, Tetrahedron Lett. 1994 35 8233
23. Yamaguchi M, Shiraishi T, Hirama M, J. Org. Chem. 1996 61 3520
24. Yamaguchi M, Igarashi Y, Reddy R S., Shiraishi T, Hirama M, Tetrahedron 1997 53 11223
25. Kochetkov K A., Harutyunyan S R., Kuzmina N A., Saveleva T F., Maleev V I., Peregudov A S., Vyskoil S, Sagiyan A S., Russ. Chem. Bull. Int. Ed. 2001 50 1620
26. Xiong Y, Wen Y, Wang F, Gao B, Liu X, Huang X, Feng X, Adv. Synth. Catal. 2007 349 2156
27. Sato A, Yoshida M, Hara S, Chem. Commun. 2008 6242
28. Liu X, Qin B, Zhou X, He B, Feng X, J. Am. Chem. Soc. 2005 127 12224
29. Li P, Yamamoto H, Chem. Commun. 2009 5412
30. For reports using chiral alkali metal binaphtholate salts, see:, Holmes I P., Kagan H B., Tetrahedron Lett. 2000 41 7453
31. Hatano M, Ikeno T, Miyamoto T, Ishihara K, J. Am. Chem. Soc. 2005 127 10776
32. Nakajima M, Orito Y, Ishizuka T, Hashimoto S, Org. Lett. 2004 6 3763
33. Ichibakase T, Orito Y, Nakajima M, Tetrahedron Lett. 2008 49 4427
34. Zhao H, Qin B, Liu X, Feng X, Tetrahedron 2007 63 6822
35. Hatano M, Horibe T, Ishihara K, J. Am. Chem. Soc. 2010 132 56
36. For reports using chiral alkali-metal phosphate salts, see:, Hatano M, Ikeno T, Matsumura T, Torii S, Ishihara K, Adv. Synth. Catal. 2008 350 1776
37. Shen K, Liu X, Cai Y, Lin L, Feng X, Chem. Eur. J. 2009 15 6008
38. For reviews on Lewis base catalysis, see:, Denmark S E., Beutner G L., Angew. Chem. Int. Ed. 2008 47 1560
39. Gawronski J, Wascinska N, Gajewy J, Chem. Rev. 2008 108 5227
40. For reviews on chiral anion, see:, Lacour J, Hebbe-Viton V, Chem. Soc. Rev. 2003 32 373
41. Lacour J, Moraleda D, Chem. Commun. 2009 7073
42. The (R)-BINOL-derived phosphoric acids 7a - g were synthesized according to the literature methods, Uraguchi D, Terada M, J. Am. Chem. Soc. 2004 126 5356
43. Yamanaka M, Itoh J, Fuchibe K, Akiyama T, J. Am. Chem. Soc. 2007 129 6756
44. Akiyama T, Katoh T, Mori K, Angew. Chem. Int. Ed. 2009 48 4226