?url_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Adc&rft.relation=http%3A%2F%2Fd-scholarship-dev.library.pitt.edu%2F19931%2F&rft.title=Stereoselective+Synthesis+of+Spirooxindole+Amides+and+Cyanohydrin+Alkyl+Ethers&rft.creator=Lu%2C+Chunliang&rft.description=A+new+family+of+spirooxindole+amides+were+synthesized+by+a+sequence+of+hydrozirconation%2C+acylation%2C+and+intramolecular+cyclization+reactions.+Three+of+the+four+possible+diastereomers+can+be+obtained+as+the+major+isomers+through+this+process.+The+spirooxindole+structure+has+many+points+for+diversification%2C+and+a+37-membered+library+was+synthesized+through+this+approach+by+collaborators.+A+comparison+with+known+compound+collections+showed+that+this+new+spirooxindole+library+possessed+good+chemical+diversity.%0D%0A%0D%0ACyanohydrin+alkyl+ethers%2C+the+key+intermediate+in+the+above+multi-component+hydrozironation+reaction%2C+were+effectively+synthesized+through+a+Br%C3%B8nsted+acid-mediated+hydrocyanation+of+vinyl+ethers.+The+enantiomerically+enriched+product+can+be+obtained+by+asymmetric+hydrocyanation+of+vinyl+ethers+catalyzed+by+a+chiral+Br%C3%B8nsted+acid%2C+and+the+catalyst%0D%0Acan+be+regenerated+by+PhOH.+As+far+as+we+know%2C+this+research+represents+the+first+example+of+chiral+Br%C3%B8nsted+acid+mediated+intermolecular+addition+of+silylated+nucleophiles+with+vinyl+ethers.+The+ion+pair+interaction+between+the+conjugate+base+of+the+chiral+Br%C3%B8nsted+acid+and+the%0D%0Aoxocarbenium+ion+was+revealed+by+computational+modeling%2C+which+explained+the+origin+of+the+enantioselectivity+and+the+substrate+scope+of+this+reaction.&rft.date=2014-01-31&rft.type=University+of+Pittsburgh+ETD&rft.type=PeerReviewed&rft.format=application%2Fpdf&rft.language=en&rft.identifier=http%3A%2F%2Fd-scholarship-dev.library.pitt.edu%2F19931%2F1%2FDissertation_Chunliang_Lu_revised_oct-23.pdf&rft.identifier=++Lu%2C+Chunliang++(2014)+Stereoselective+Synthesis+of+Spirooxindole+Amides+and+Cyanohydrin+Alkyl+Ethers.++Doctoral+Dissertation%2C+University+of+Pittsburgh.++++(Unpublished)++