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filingDate 1998-07-13-04:00^^<http://www.w3.org/2001/XMLSchema#date>
grantDate 2002-02-12-04:00^^<http://www.w3.org/2001/XMLSchema#date>
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publicationDate 2002-02-12-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber US-6346652-B1
titleOfInvention Asymmetric ring-closing metathesis reactions involving achiral and meso substrates
abstract A composition and method for the catalytic conversion of a racemic mixture of dienes to a cyclic olefin by a ring-closing metathesis (RCM) reaction are disclosed. The composition, a transition metal complex with an M=C reaction site, contains a bidentate dialkoxide of at least 80% optical purity. Because the M=C reaction site is of a sufficient shape specificity, conferred in part by the dialkoxide of sufficient rigidity and a M=N-R1 site, reacting the composition with a mixture of two enantiomeric dienes results in an olefin metathesis product that has at least a 50% enantiomeric excess of one enantiomer in the mixture. A method is also provided for reacting a composition with a racemic diene mixture to generate a metathesis product that has an enantiomeric excess of at least 50%. Methods are also provided for catalytic enantioselective desymmetrization. One method involves an olefin metathesis reaction with a molecular substrate having a plane of symmetry to form a product free of a plane of symmetry. Another method provides a desymmetrization reaction to occur in the absence of solvent. A method for producing quaternary carbon centers through a desymmetrization reaction is also described.
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http://rdf.ncbi.nlm.nih.gov/pubchem/substance/SID247844576
http://rdf.ncbi.nlm.nih.gov/pubchem/compound/CID11106001
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http://rdf.ncbi.nlm.nih.gov/pubchem/substance/SID141968873
http://rdf.ncbi.nlm.nih.gov/pubchem/substance/SID127427561
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http://rdf.ncbi.nlm.nih.gov/pubchem/substance/SID248910662
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http://rdf.ncbi.nlm.nih.gov/pubchem/compound/CID22948203
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http://rdf.ncbi.nlm.nih.gov/pubchem/substance/SID136001996
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Total number of triples: 365.