Highly efficient chiral copper Schiff-base catalyst for asymmetric cyclopropanation of 2,5-dimethyl-2,4-hexadiene

Tetrahedron

Volumn 60, Issue 36, 2004, Pages 7835-7843

  Itagaki, Makoto ^a   Hagiya, Koji ^a   Kamitamari, Masashi ^a   Masumoto, Katsuhisa ^a   Suenobu, Katsuhiro ^a   Yamamoto, Yohsuke ^b  

^a SUMITOMO CHEMICAL CO LTD   (Japan)

^b HIROSHIMA UNIVERSITY   (Japan)

Author keywords

2,5 Dimethyl 2,4 hexadiene; Asymmetric cyclopropanation; Copper Schiff base; Diazoacetate; Lewis acid

Indexed keywords

ALKADIENE; AMINOALCOHOL; COPPER; COPPER ACETATE; DIAZOACETIC ACID ETHYL ESTER; LEWIS ACID; SALICYLALDEHYDE; SCHIFF BASE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; CHIRALITY; CYCLOPROPANATION; ENANTIOSELECTIVITY; PRIORITY JOURNAL; STRUCTURE ANALYSIS; TEMPERATURE;

EID: 4043101165     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.06.073     Document Type: Article

References (13)

1. Lebel H., Marcoux J.-F., Molinaro C., Charette A.B. Chem. Rev. 103:2003;977
2. Doyle M.P., McKervey M.A., Ye T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds. 1998;Wiley, New York
3. Singh V.K., Gupta A.D., Sekar G. Synthesis. 1997;137
4. Doyle M.P., Protopopova M.N. Tetrahedron. 54:1998;7919
5. Aratani T., Yoneyoshi Y., Nagase T. Tetrahedron Lett. 1977;2599
6. Aratani T., Yoneyoshi Y., Nagase T. Tetrahedron Lett. 1975;1707
7. Aratani T. Pure Appl. Chem. 57:1985;1839
8. Lowenthal R.E., Masamune S. Tetrahedron Lett. 32:1991;7373
9. Kanemasa S., Hamura S., Harada E., Yamamoto H. Tetrahedron Lett. 35:1994;7985
10. Sanders C.J., Gillespie K.M., Scott P. Tetrahedron: Asymmetry. 12:2001;1055
11. Li Z., Liu G., Zheng Z., Chen H. Tetrahedron. 56:2000;7187
12. In Ref. 11, the yield of the cyclopropanation of the diene was not recorded
13. Suenobu K., Itagaki M., Nakamura E. J. Am. Chem. Soc. 126:2004;7271