Highly enantioselective benzylic hydroxylation with concave type of (salen)manganese(III) complex

Tetrahedron

Volumn 54, Issue 34, 1998, Pages 10017-10028

  Hamada, Tetsuya ^a   Irie, Ryo ^a   Mihara, Jun ^a   Hamachi, Kiyoe ^a   Katsuki, Tsutomu ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BENZILIC ACID; MANGANESE DERIVATIVE; SALEN MANGANESE(III) COMPLEX; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; HYDROXYLATION; OPTICAL ROTATION; OXIDATION; PRIORITY JOURNAL; REACTION TIME; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

EID: 0032552048     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00603-6     Document Type: Article

References (36)

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4. 4. In the preliminary communication, we reported that hydroxylation of 1,1-dimethylindan using 1 as the catalyst at 10 °C for 1.5 h gave the alcohol of 64% ee. This value was reproducible in errors of ±1.5% as long as the same mechanical stirrer was used. Since iodosylbenzene is sparingly soluble in organic solvent, oxidation rate is dependent on the efficiency of stirring and enantioselectivity of the reaction is affected by reaction time, reaction temperature, and efficiency of stirring. The slight difference in the enantiomeric excesses of the alcohols obtained in the preliminary and present reports is probably attributed to use of the different stirrer and the different lot of iodosylbenzene. It was confirmed that the 61% ee observed in this study was also reproducible in errors of ±1.5%, as long as we used the same stirrer and the same lot of iodosylbenzene.
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