Mn-salen catalyzed asymmetric epoxidation of 1,3-cycloalkadienes and dialkylsubstituted Z-olefins

Synlett

Volumn 1995, Issue 8, 1995, Pages 827-828

  Mikame, Daisuke ^a   Hamada, Tetsuya ^a   Irie, Ryo ^a   Katsuki, Tsutomu ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

(salen)manganese(III) complex; 1,3 cycloalkadiene; asymmetric epoxidation

Indexed keywords

EID: 85013986962     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-1995-5105     Document Type: Article

References (9)

1. Katsuki, T. Chem. Coord. Rev., 1995, 140, 189.
2. Sasaki, H.; Irie, R.; Katsuki, T. Synlett, 1994, 356.
3. Sasaki, H.; Irie, R.; Hamada, T.; Suzuki, K.; Katsuki, T. Tetrahedron, 1994, 50, 11827.
4. Fukuda, T.; Irie, R.; Katsuki, T. Synlett, 197.
5. Hosoya, N.; Hatayama, A.; Yanai, K., Fujii, H., Irie, R.; Katsuki, T. Synlett, 1993, 641.
6. Hamada, T.; Irie, R.; Katsuki, T. Synlett, 1994, 479.
7. Chang, S.; Heid, R. M.; Jacobsen, E. N. Tetrahedron Lett., 1994, 35, 669. High enantioselectivity has been observed in the epoxidation of 2-acetoxy-l,3-cyclohexadiene, wherein the intensified electronic and steric repulsion between the salenbenzene ring and the olefin by the presence of the acetoxy group is considered to contribute to increasing enantioselectivity (see also ref. 3b).
8. Marino, J. P.; Jaen, J. C. Tetrahedron Lett., 1983,24, 441.
9. Jacobsen, E. N.; Zhang, W.; Guller, M. L. J. Am. Chem. Soc., 1991,113, 6703.