Source:http://linkedlifedata.com/resource/pubmed/id/17441160
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rdf:type | |
lifeskim:mentions | |
pubmed:issue |
2
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pubmed:dateCreated |
2007-4-18
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pubmed:abstractText |
The full details of the asymmetric epoxidation of alpha,beta-unsaturated esters catalyzed by yttrium complexes with biaryldiol ligands are described. An yttrium-biphenyldiol catalyst, generated from Y(OiPr)3-biphenyldiol ligand-triphenylarsine oxide (1:1:1), is suitable for the epoxidation of various alpha,beta-unsaturated esters. With this catalyst, beta-aryl alpha,beta-unsaturated esters gave high enantioselectivities and good yields (< or = 99% ee). The reactivity of this catalyst is good, and the catalyst loading could be decreased to as little as 0.5-2 mol % (the turnover number was up to 116), while high enantiomeric excesses were maintained. For beta-alkyl alpha,beta-unsaturated esters, an yttrium-binol catalyst, generated from Y(OiPr)3-binol ligand-triphenylphosphine oxide (1:1:2), gave the best enantioselectivities (< or = 97% ee). The utility of the epoxidation reaction was demonstrated in an efficient synthesis of (-)-ragaglitazar, a potential antidiabetes agent.
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pubmed:language |
eng
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pubmed:journal | |
pubmed:citationSubset |
IM
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pubmed:chemical |
http://linkedlifedata.com/resource/pubmed/chemical/Epoxy Compounds,
http://linkedlifedata.com/resource/pubmed/chemical/Esters,
http://linkedlifedata.com/resource/pubmed/chemical/Oxazines,
http://linkedlifedata.com/resource/pubmed/chemical/Phenylpropionates,
http://linkedlifedata.com/resource/pubmed/chemical/Yttrium,
http://linkedlifedata.com/resource/pubmed/chemical/ragaglitazar
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pubmed:status |
MEDLINE
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pubmed:month |
Feb
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pubmed:issn |
1861-471X
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pubmed:author | |
pubmed:issnType |
Electronic
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pubmed:day |
5
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pubmed:volume |
2
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pubmed:owner |
NLM
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pubmed:authorsComplete |
Y
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pubmed:pagination |
257-64
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pubmed:meshHeading | |
pubmed:year |
2007
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pubmed:articleTitle |
Catalytic asymmetric epoxidation of alpha,beta-unsaturated esters with chiral yttrium-biaryldiol complexes.
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pubmed:affiliation |
Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
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pubmed:publicationType |
Journal Article,
Research Support, Non-U.S. Gov't
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