Unusual solvent-effect in stereochemistry of asymmetric epoxidation using a (salen)chromium(III) complex as a catalyst

Tetrahedron Letters

Volumn 38, Issue 2, 1997, Pages 251-254

  Imanishi, Hirotoshi ^a   Katsuki, Tsutomu ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CHROMENE DERIVATIVE; STYRENE DERIVATIVE;

ARTICLE; CATALYSIS; DRUG OXIDATION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031021842     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02274-5     Document Type: Article

References (22)

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4. (Salen)chromium(III) complex (1) was synthesized from the corresponding Schiff base (reference 15) according to Kochi's procedure (reference 6).
5. In the case of manganese catalysts, complex 2 shows higher enantioselectivity than 4.
6. The reaction without PPNO in acetone at 0°C also gave the (3R,4R)-epoxide of 52% ee, while that in benzene at rt gave the (3S,4S)-epoxide of 60% ee.
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14. Differing from PhIO, pentafluoroiodosylbenzene has been reported to oxidize an iron-porphyrin complex to the corresponding oxo species smoothly (reference 7). Therefore, we examined the epoxidation of p-chlorostyrene using these two oxidants but both reactions in toluene and acetonitrile showed the same sense and similar level of enantioselectivity, respectively, suggesting that these two oxidants gave the same active species.
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19. Epoxidation of p-nitrostyrene at 0 °C using complex 2 or the structurally related Mn-salen complex shows enantioselectivity lower than 30% ee due to the epimerization at the stage of the radical intermediate (reference 11la).
20. Mn-salen catalyzed epoxidation of styrene derivatives at -78 °C using m-CPBA as an oxidant has been reported to show high enantioselectivity: Palucki, M.; Pospisil, P. J.; Zhang, W.; Jacobsen, E. N. J. Am. Chem. Soc. 1994, 116, 9333-9334.
21. Groves, J. T.; Myers, R. S. J. Am. Chem. Soc. 1983, 105, 5791-5796.
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