Photo-controlled Lewis acidity: Chiral (ON)Ru-salen catalyzed hetero Diels-Alder reaction and kinetic resolution of racemic epoxides

Synlett

Volumn , Issue 7, 1999, Pages 1160-1162

  Mihara, Jun ^a   Hamada, Tetsuya ^a   Takeda, Tsuyoshi ^a   Irie, Ryo ^a   Katsuki, Tsutomu ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

(ON+)(salen)ruthenium(II) complex; Hetero Diels Alder reaction; Kinetic resolution of racemic epoxides; Lewis acid catalysis; Photo activation

Indexed keywords

ACETIC ACID DERIVATIVE; EPOXIDE; ETHER; NAPHTHALENE DERIVATIVE; RUTHENIUM COMPLEX;

ARTICLE; CATALYSIS; CATALYST; CHIRALITY; CYCLIZATION; EPOXIDATION; LIGHT; PHOTOACTIVATION; RACEMIC MIXTURE;

EID: 0032770159     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2781     Document Type: Article

References (14)

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2. Ford, P. C.; Bourassa, J.; Miranda, K.; Lee, B.; Lorkovic, I.; Boggs, S.; Kudo, S.; Laverman, L. Coord. Chem. Rev. 1998, 171, 185-202.
3. Noyori, R. "Asymmetric Catalysis in Organic Synthesis" John Wiley & Sons, New York, 1994.
4. a) Katsuki, T. J. Mol. Cat. A: Chem. 1996, 113, 87-107.
5. b) Ito, Y. N.; Katsuki, T. Bull. Chem. Soc. Jpn. 1999, 72, 603-619.
6. Bosnich et al. has been reported Diels-Alder reaction using achiral cationic (NO)Ru-salen as a catalyst: Odenkirk, W.; Rheingold, A. L.; Bosnich, B. J. Am. Chem. Soc. 1992, 114, 6392-6398.
7. a) For asymmetric hetero Diels-Alder reactions, see: Waldmann, H. Synthesis 1994, 535-551.
8. b) For the Cr-salen-catalyzed reaction, see: Schaus, S. E.; Brånalt, J.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 403-405.
9. 6 according to the reference 5.
10. For kinetic resolution of epoxides, see: a) Asami, M. J. Synth. Org. Chem., Jpn. 1996, 54, 188-199.
11. b) Tokunaga, M.; Larrow, J. F.; Kakiuchi, F.; Jacobsen, E. N. Science 1997, 277, 936-938.
12. Yamashita, Y.; Katsuki, T. Synlett 1995, 829-830.
13. As described in the preceding communication, the produced cpoxide in the epoxidation of dihydronaphthalene suffered from the undesirable decomposition under the reaction conditions. This is probably attributable to that the produced epoxide is coordinated to the Lewis acidic ruthenium ion and, therefore, the epoxide is much more subject to the decomposition.
14. The mechanism of the photo enhancement of the Lewis acidity is not clear at present but the photo-induced ligand dissociation is considered to be responsible for this phenomenon as described in Synlett 1999, 1160