http://rdf.ncbi.nlm.nih.gov/pubchem/patent/US-7582764-B2

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filingDate 2006-05-26-04:00^^<http://www.w3.org/2001/XMLSchema#date>
grantDate 2009-09-01-04:00^^<http://www.w3.org/2001/XMLSchema#date>
inventor http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_fa3781111c96cbfba8e3f391af687d71
http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_80353567fffce0f8660b354d25ec403e
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publicationDate 2009-09-01-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber US-7582764-B2
titleOfInvention Asymmetric carbon-carbon-bond-forming reactions catalyzed by bifunctional cinchona alkaloids
abstract One aspect of the present invention relates to quinine-based and quinidine-based catalysts. In certain embodiments, the quinine-based and quinidine-based catalysts contain a hydroxy group at the 6′ position. In certain embodiments, the quinine-based and quinidine-based catalysts contain an O-aryl group or an O-aroyl group at the C9 position. In certain embodiments, the quinine-based and quinidine-based catalysts contain an optionally substituted O-diazene group or an optionally substituted O-benzoyl group at the C9 position. In certain embodiments, the quinine-based and quinidine-based catalysts contain a thiourea at the C9 position. In certain embodiments, the quinine-based and quinidine-based catalysts contain an NH(═S)NH-aryl group at the C9 position. Another aspect of the present invention relates to a method of preparing a chiral, non-racemic compound from a prochiral electron-deficient alkene or prochiral imine, comprising the step of: reacting a prochiral alkene or imine with a nucleophile in the presence of a catalyst; thereby producing a chiral, non-racemic compound; wherein said catalyst is a derivatized quinine or quinidine. In certain embodiments, the nucleophile is a malonate or β-ketoester. In certain embodiments the nucleophile is an alkyl or aryl or aralkyl 2-cyano-2-alkylacetate. In certain embodiments the nucleophile is an alkyl or aryl or aralkyl 2-cyano-2-alkylacetate. n Another aspect of the present invention relates to a method of kinetic resolution, comprising the step of: reacting a racemic aldehyde or racemic ketone with a nucleophile in the presence of a derivatized quinine or quinidine, thereby producing a non-racemic, chiral compound. In certain embodiments, the kinetic resolution is dynamic.
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priorityDate 2004-06-03-04:00^^<http://www.w3.org/2001/XMLSchema#date>
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Total number of triples: 378.