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1、HydrogenBondingCatalysisandRedoxNeutralCascadeReactionsByMatthewK.VecchioneAThesissubmittedtotheGraduateSchool-NewBrunswickRutgers,theStateUniversityofNewJerseyInpartialfulfillmentoftherequirementsForthedegreeofMasterofScienceGraduatePrograminChemistryWrittenu
2、nderthedirectionofDr.DanielSeidelAndapprovedby--------------------------------------------------------------------------------------------------------------------------------------------NewBrunswick,NewJersey[January2011]ABSTRACTOFTHETHESISHydrogenBondingCatal
3、ysisandRedoxNeutralCascadeReactionsByMatthewKyleVecchioneThesisDirector:Dr.DanielSeidelMythesisisdividedintotwoparts;hydrogenbondingcatalysisandredoxneutralcascadereactions.Relatingtohydrogenbondingcatalysis,Iwassuccessfulinperforminganadditionofisothiocyanato
4、imidestoα-ketoesters,withtheultimategoalofsynthesizingbeta-hydroxy-alpha-aminoacids.Thenecessityofmoreconventionalmeanstodevelopcatalytic,enantioselective,anddiastereoselectiveroutestothesemoietiescanbeseenintheirpresenceinmanynaturalproducts,includingvancomyc
5、in.Redoxneutralchemistryhasgainedstrongpopularityduetoitsadvantageousqualities,including:itsgreen,environmental-friendlycharacteristics,lackofusingexpensiveorharmfuloxidantsandreductants,andabilitytobuildupmolecularcomplexitywithlimitednumberofsteps.Underthisb
6、ranchofchemistry,Iwasabletodevelopanacid-assistedindoleadditiontoortho-aminoaldehydesleadingtothesynthesisofquinolinederivatives.Thesecompounds,althoughnotstudiedextensively,havebeendiscoveredtobepotentsirtuinproteininhibitorsandprecursorstonumberofsimplenatur
7、alproducts,includingcryptosanguinolentine.Afurtherstudyevaluatingsecondaryaminobenzaldehydesandindoleshowsthatthesynthesisoftheantimalarialagentneocryptolepinecouldbeeasilyiiachieved.Thissimplemethodologyalsomakesitpossibletosynthesizeanaloguesofthisimportantn
8、aturalproduct.iiiTableofContentsAbstractii–iiiListoffiguresviListofschemesvii-xListoftablesxiChapter1–HydrogenBondingCatalysis?-hydroxy-α-aminoacids1,17Ideaofbifunctionalcatalysis2
