Highly cis- and enantioface-selective cyclpropanation using (R,R)-Ru- salen complex: Solubility dependent enantioface selection

Synlett

Volumn , Issue 11, 1999, Pages 1793-1795

  Uchida, Tatsuya ^a   Irie, Ryo ^a   Katsuki, Tsutomu ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

(ON+)(salen)ruthenium(II) complex; Cis selectivity; Cyclopropanation; Photo activation

Indexed keywords

CYCLOPROPANE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; PHOTOACTIVATION; SOLUBILITY; STEREOCHEMISTRY;

EID: 0032705876     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2955     Document Type: Article

References (17)

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2. b) Ito, Y. N.; Katsuki, T. Bull. Chem. Soc. Jpn. 1999, 72, 603-619.
3. Uchida, T.; Irie, R.; Katsuki, T. Synlett 1999, 1163-1165.
4. Punniyamurthy, T.; Irie, R.; Katsuki, T.; Akita, M.; Moro-oka, Y. Synlett, 1999, 1049-1052.
5. For the review of metal-catalyzed asymmetric cyclopropanation, see: a) Doyle, M. P.; McKervey, M. A.; Ye, T. "Modern Catalytic Methods for Organic Synthesis with diazo Compounds," John Wiley & Sons (New York), 1998.
6. b) Doyle, M. P.; Protopopova, M. N. Tetrahedron 1998, 54, 7919-7946.
7. Padwa, A.; Hornbuckle, S. F. Chem. Rev. 1991, 91, 263-309.
8. For ruthenium-catalyzed asymmetric cyclopropanation, see: a) Nishiyama, H.; Itoh, Y.; Matsumoto, H.; Park, S.-B.; Itoh, K. J. Am. Chem. Soc. 1994, 116, 2223-2224.
9. b) Nishiyama, H.; Itoh, Y.; Sugawara, Y.; Matsumoto, H.; Aoki, K.; Itoh, K. Bull. Chem. Soc. Jpn. 1995, 68, 1247-1262.
10. Frauenkron, M.; Berkessel, A. Tetrahedron Lett. 1997, 38, 7175-7176.
11. Lo, W.-C.; Che, C.-M.; Cheng, K.-F.; Mak, T. C. W. Chem. Commun. 1997, 1205-1206.
12. e) Song, J.-H.; Cho, D.-J.; Kim, Y.-H.; Kim, T.-J. Inorg. Chem. 1999, 38, 893-896.
13. Catalyst has been considered to be activated by dissociation of the apical ligand which is promoted by irradiation (reference 2 and reference 10).
14. We observed that non-catalyzed reaction actually occurred in the absence of the catalyst 1 (reference 2).
15. The yield of a mixture of maleic and fumaric acid esters was 32%, when the reaction was performed in THF-styrene (10/1).
16. The reaction with ethyl α-diazoacetate in the presence of the catalyst 1 (5 mol %, based on α-diazoacetate used) at room temperature in a mixture of THF and styrene (2/1) under irradiation of incandescent light also proceeded with high cis-and enantio-selectivity [cis : trans = 93 : 7, 95% ee (cis-isomer)].
17. It has been reported that flash photolysis of Ru(TPP)(NO)Cl presumably generates a transient species, Ru(TPP)Cl: Lorkovic, I. M.; Miranda, K. M.; Lee, B.; Bernhard, S.; Schoonover, J. R.; Ford, P. C. J. Am. Chem. Soc. 1998, 120, 11674-11683.