Development of C-C bond formation and asymmetric reactions catalyzed by N-heterocyclic carbenes

Yakugaku Zasshi

Volumn 128, Issue 8, 2008, Pages 1179-1185

  Suzuki, Yumiko ^a  

^a UNIVERSITY OF SHIZUOKA   (Japan)

Author keywords

Asymmetric acylation; Cyanosilylation; Kinetic resolution; N heterocyclic carbene; Nucleophilic aroylation; Organocatalyst

Indexed keywords

CARBENOID; IMIDAZOLE DERIVATIVE; N HETEROCYCLIC CARBENE;

ACYLATION; CATALYST; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; REVIEW;

ACYLATION; ALCOHOLS; ALDEHYDES; CARBON; CATALYSIS; CHEMISTRY, ORGANIC; HETEROCYCLIC COMPOUNDS; METHANE;

EID: 48349106826     PISSN: 00316903     EISSN: 13475231     Source Type: Journal    
DOI: 10.1248/yakushi.128.1179     Document Type: Review

References (40)

1. Wanzlick H.-W., Schikora E., Angew. Chem., 72, 494 (1960).
2. Wanzlick H.-W., Kleiner H.-J., Angew. Chem., 73, 493 (1961).
3. Wanzlick H.-W., Angew. Chem., 74, 129-134 (1962).
4. Arduengo III, A. J., Harlow R. L., Kline M. A., J. Am. Chem. Soc., 113, 361-363 (1991).
5. Arduengo III, A. J., Acc. Chem. Res., 32, 913-921 (1999).
6. Herrrmann W. A., Kocher C., Angew. Chem. Int. Ed. Engl., 36, 2162-2187 (1997).
7. Ukai T., Tanaka R., Dokawa S., J. Pharm. Soc. Jpn., 63, 296-300 (1943).
8. Mizuhara S., Handler P., J. Am. Chem. Soc., 76, 571-573 (1954).
9. Breslow R., J. Am. Chem. Soc., 80, 3719-3726 (1958).
10. "N-Heterocyclic Carbenes in Synthesis," ed. by S. P. Nolan, WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim, 2006.
11. Enders D., Balensiefer T., Acc. Chem. Res., 37, 534-541 (2004).
12. Nair V., Bindu S., Sreekumar V., Angew. Chem. Int. Ed., 43, 5130-5135 (2004).
13. Marion N., Díez-González S., Nolan S. P., Angew. Chem. Int. Ed., 46, 2988-3000 (2007).
14. Enders D., Niemeier O., Henseler A., Chem. Rev., 107, 5606-5655 (2007).
15. Suzuki Y., J. Syn. Org. Chem. Jpn., 66, 377-386 (2008).
16. Higashino T., Takemoto M., Miyashita A., Hayashi E., Chem. Pharm. Bull., 33, 1395-1399 (1985).
17. Miyashita A., Matsuda H., Iijima C., Higashino T., Chem. Pharm. Bull., 38, 1147-1152 (1990).
18. Miyashita A., Matsuda H., Iijima C., Higashino T., Chem. Pharm. Bull., 40, 43-48 (1992).
19. Miyashita A., Matsuda H., Suzuki Y., Iwamoto K., Higashino T., Chem. Pharm. Bull., 42, 2017-2022 (1994).
20. Miyashita A., Obae K., Suzuki Y., Iwamoto K., Oishi E., Higashino T., Heterocycles, 45, 2159-2173 (1997).
21. Miyashita A., Suzuki Y., Iwamoto K., Higashino T., Chem. Pharm. Bull., 46, 390-399 (1998).
22. Miyashita A., Suzuki Y., Iwamoto K., Oishi E., Higashino T., Heterocycles, 49, 405-413 (1998).
23. Suzuki Y., Toyota T., Imada F., Sato M., Miyashita A., Chem. Commun., 2003, 1314-1315.
24. Suzuki Y., Toyota T., Miyashita A., Sato M., Chem. Pharm. Bull. 54, 1653-1658 (2006).
25. Song J. J., Gallou F., Reeves J. T., Tan Z., Yee N. K., Senanayake C. H., J. Org. Chem., 71, 1273-1276 (2006).
26. Fukuda Y., Maeda Y., Ishii S., Kondo K., Aoyama T., Synthesis, 4, 589-590 (2006).
27. Kano T., Sasaki K., Konishi T., Mii H., Maruoka K., Tetrahedron Lett., 47, 4615-4618 (2006).
28. Suzuki Y., Md. A. B., Muramatsu K., Sato M., Tetrahedron, 62, 4227-4231 (2006).
29. Tian S.-K., Hong R., Deng L., J. Am. Chem. Soc., 125, 9900-9901 (2003).
30. Wu J., Sun X., Ye S., Sun W., Tetrahedron Lett., 47, 4813-4816 (2006).
31. Song J. J., Tan Z., Reeves J. T., Yee N. K., Senanayake C. H., Org. Lett., 6, 1013-1016 (2007).
32. Reynolds T. E., Stern C. A., Scheidt K. A., Org. Lett., 9, 2581-2584 (2007).
33. Grasa G. A., Kissling R. M., Nolan S. P., Org. Lett., 4, 3583-3586 (2002).
34. Nyce G. W., Lamboy J. A., Connor E. F., Waymouth R. M., Hedrick J. L., Org. Lett., 4, 3587-3590 (2002).
35. Suzuki Y., Yamauchi K., Muramatsu K., Sato M., Chem. Commun., 2004, 2770-2771.
36. Suzuki Y., Muramatsu K., Yamauchi K., Sato M., Tetrahedron, 62, 302-310 (2006).
37. Kano T., Sasaki K., Maruoka K., Org. Lett., 7, 1347-1349 (2005).
38. Movassaghi M., Schmidt M. A., Org. Lett., 7, 2453-2456 (2005).
39. Lai C.-L., Lee H. M., Hu C.-H., Tetrahedron Lett., 46, 6265-6270 (2005).
40. Suzuki Y., Ota S., Fukuta Y., Ueda Y., Sato M., J. Org. Chem., 73, 2420-2423 (2008).