Facile route to benzils from aldehydes via NHC-catalyzed benzoin condensation under metal-free conditions

Tetrahedron Letters

Volumn 51, Issue 13, 2010, Pages 1786-1789

  Shimakawa, Yuuki ^a   Morikawa, Takashi ^a   Sakaguchi, Satoshi ^a  

^a KANSAI UNIVERSITY   (Japan)

Author keywords

Benzil; Benzoin; N Heterocyclic carbene; Organocatalyst; Oxidation

Indexed keywords

1,2 DICARBONYL DERIVATIVE; 1,2 DIKETONE; ALDEHYDE DERIVATIVE; AZOLIUM SALT; BENZIL; BENZOIN; CARBENOID; DIKETONE; N HETEROCYCLIC CARBENE; SODIUM CHLORIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; ONE POT SYNTHESIS; OXIDATION; ROOM TEMPERATURE;

EID: 77149133399     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.01.103     Document Type: Article

References (34)

1. Rong F., Chow S., Yan S., Larson G., Hong Z., and Wu J. Bioorg. Med. Chem. Lett. 17 (2007) 1663-1666
2. Ams M.R., and Wilcox C.S. J. Am. Chem. Soc. 129 (2007) 3966-3972
3. Selected recent publications:. Uyanik M., Akakura M., and Ishihara K. J. Am. Chem. Soc. 131 (2009) 251-262
4. Heirtzler F., Neuburger M., and Kulike K. J. Chem. Soc., Perkin Trans. 1 (2002) 809-820
5. Chang H.S., Woo J.C., Lee K.M., Ko Y.K., Moon S.-S., and Kim D.-W. Synth. Commun. 32 (2002) 31-35
6. Selected recent publications:. Ren W., Xia Y., Ji S.-J., Zhang Y., Wan X., and Zhao J. Org. Lett. 11 (2009) 1841-1844
7. Niu M., Fu H., Jiang Y., and Zhao Y. Synthesis (2008) 2879-2882
8. Wan Z., Jones C.D., Mitchell D., Pu J.Y., and Zhang T.Y. J. Org. Chem. 71 (2006) 826-828
9. Katritzky A.R., Zhang D., and Kirichenko K. J. Org. Chem. 70 (2005) 3271-3274 and references cited therein
10. Selected reviews:. Díez-González S., Marion N., and Nolan S.P. Chem. Rev. 109 (2009) 3612-3676
11. Hahn F.E., and Jahnke M.C. Angew. Chem., Int. Ed. 47 (2008) 3122-3172
12. In: Glorius F. (Ed). Topics in Organometallic Chemistry Vol. 21 (2007), Springer, Berlin
13. Douthwaite R.E. Coord. Chem. Rev. 251 (2007) 702-717
14. Kantchev E.A.B., O'Brien C.J., and Organ M.G. Angew. Chem., Int. Ed. 46 (2007) 2768-2813
15. Herrmann W.A. Angew. Chem., Int. Ed. 41 (2002) 1290-1309
16. Selected reviews:. Enders D., Niemeier O., and Henseler A. Chem. Rev. 107 (2007) 5606-5655
17. Clavier H., and Nolan S.P. Annu. Rep. Prog. Chem., Scet. B. 103 (2007) 193-222
18. Dvorak C.A., and Rawal V.H. Tetrahedron Lett. 39 (1998) 2925-2928
19. Knight R.L., and Leeper F.J. Tetrahedron Lett. 38 (1997) 3611-3614
20. Enders D., and Kallfass U. Angew. Chem., Int. Ed. 41 (2002) 1743-1745
21. Knight R.L., and Leeper F.J. J. Chem. Soc., Perkin Trans. 1 (1998) 1891-1893
22. Xu L.-W., Gao Y., Yin J.-J., Li L., and Xia C.-G. Tetrahedron Lett. 46 (2005) 5317-5320
23. Iwamoto K., Hamaya M., Hashimoto N., Kimura H., Suzuki Y., and Sato M. Tetrahedron Lett. 47 (2006) 7175-7177
24. Sakaguchi S., Yoo K.S., O'Neill J., Lee J.H., Stewart T., and Jung K.W. Angew. Chem., Int. Ed. 47 (2008) 9326-9329
25. Lee J.H., Yoo K.S., Park C.P., Olsen J.M., Sakaguchi S., Prakash G.K.S., Mathew T., and Jung K.W. Adv. Synth. Catal. 351 (2009) 563-568
26. Sakaguchi S., Kawakami M., O'Neill J., Yoo K.S., and Jung K.W. J. Organomet. Chem. 695 (2010) 195-200
27. Yoo K., O'Neill J.S., Sakaguchi S., Giles R., Lee J.H., and Jung K.W. J. Org. Chem. 75 (2010) 95-101
28. Okamoto M., Yamamoto Y., and Sakaguchi S. Chem. Commun. (2009) 7363-7365
29. Miyashita A., Suzuki Y., Iwamoto K., and Higashino T. Chem. Pharm. Bull. 42 (1994) 2633-2635
30. Jing X., Pan X., Li Z., Shi Y., and Yan C. Synth. Commun. 39 (2009) 492-496
31. Unfortunately, the enantio excess of the product 2b was low (10% ee). To the best of our knowledge, however, little paper concerned with asymmetric benzoin reaction by the use of a chiral imidazolium salt was known:. Orlandi S., Caporale M., Benaglia M., and Annunziata R. Tetrahedron: Asymmetry 14 (2003) 3827-3830
32. Struble J.R., Kaeobamrung J., and Bode J.W. Org. Lett. 10 (2008) 957-960
33. Aggarwal V.K., Emme I., and Mereu A. Chem. Commun. (2002) 1612-1613
34. Háda V., Tungler A., and Szepesy L. J. Catal. 209 (2002) 472-479