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1、Chem.Rev.1999,99,1469-14801469NucleophilicAdditionsto4,4-Disubstituted2,5-Cyclohexadienones:CanDipoleEffectsControlFacialSelectivity?PeterWipf*andJae-KyuJungDepartmentofChemistry,UniversityofPittsburgh,Pittsburgh,Pennsylvania15260ReceivedAugust19,1998(RevisedManuscriptReceivedDecember7,1998)Conten
2、tsI.IntroductionandBackground1469II.PreliminaryExperimentalDataforNucleophilic1471AdditionstoCyclohexadienonesIII.1,2-AdditionsofGrignardandOrganolithium1473Reagentsto4,4-Disubstituted2,5-CyclohexadienonesIV.ElectrostaticvsStereoelectronicControl1474V.QuantitativeCorrelationbetweenFacial1475Select
3、ivityandDipoleMomentVI.SolventEffectsandDesignofaLong-Range1476ElectrostaticChiralAuxiliaryVII.NucleophilicAdditionstoNaphthodiquinones1477VIII.Conclusions1479IX.Acknowledgments1479PeterWipfreceivedhisDiplomain1984andhisPh.D.in1987fromtheUniversityofZu¨richunderthedirectionofProf.HeinzHeimgartner.
4、HisX.ReferencesandNotes1479postdoctoralworkasaSwissNSFPostdoctoralFellowwithProf.RobertE.IrelandledhimtotheUniversityofVirginiainCharlottesville.In1990,hejoinedthefacultyattheUniversityofPittsburghasanAssistantI.IntroductionandBackgroundProfessorandwaspromotedtoAssociateProfessorin1995andProfessor
5、in1997.HisresearchinterestsfocusonthetotalsynthesisofnaturalªItisacapitalmistaketotheorisebeforeoneproducts,heterocyclicandorganometallicchemistry,andcombinatorialhasdata.Insensiblyonebeginstotwistfactschemistry.AmonghisrecentawardsaretheArthurC.CopeScholarAward(1998),theAkronSectionACSAward(1998)
6、,andaChancellor’stosuittheories,insteadoftheoriestosuitfacts.º1DistinguishedResearchAward(1997).(SherlockHolmes,AScandalinBohemia)Thedesymmetrizationofthetwofacesofaplanarcarbonylgroup2hasemergedasoneofthemostimportantparadigmsinthefieldofstereoselectivesynthesissinceCram3proposedamodeltopredictth
7、efacialselectivityofnucleophilicadditiontoR-chiralaldehydesandketones.TheCrammodelcorrectlypredictsthemajordiastereomerofmostasymmetricadditionreactions,withthenotableexceptionofGrignardadditionstoR-chloroketones
