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1、6SupplementaryMaterial(ESI)forChemicalCommunicationsThisjournalis©TheRoyalSocietyofChemistry2002ElectronicSupplementaryInformationPlanarandcentralchiral[2.2]paracyclophane-basedN,O-ligandsashighlyactivecatalystsinthediethylzincadditiontoaldehydesStefanDahmen†andStef
2、anBräse*,§Kekulé-InstitutfürOrganischeChemieundBiochemiederRheinischenFriedrich-Wilhelms-UniversitätBonn,Gerhard-Domagk-Strasse1,D-53121Bonn,Germany,andInstitutfürOrganischeChemiederRheinisch-WestfälischenTechnischenHochschuleAachen,Professor-Pirlet-Straße1,D-52074A
3、achen,Germanybraese@uni-bonn.de1GeneralAllchemicalsandsolventswereusedasreceivedunlessotherwisestated.THF(Na,benzophenone),toluene(Na,benzophenone),CH2Cl2(CaH2),hexane(CaH2),methanol(Mg)weredistilledunderargonfromthedryingagentindicated.1Hand13CNMRspectrawererecorde
4、dwithaVarianVXR300(300/75 MHz),VarianUnity500(500/125 MHz),VarianInova(400/100 MHz)orGemini300S(300/75 MHz)instrument.Abbreviationsfor1HNMR:s=singlet,d=doublet,t=triplet,m=multiplet,Ar=aromatic;abbreviationsfor13CNMR:p=primary,s=secondary,t=tertiary,q=quaternarycarb
5、onatomasdeterminedbyATPandDEPTexperiments.Preparativeliquidchromatographywasperformedonstraightphasesilicagel(Merck60,230–400mesh,0.040–0.063mm)oronneutralaluminumoxide(Merck,60PF254TypeE),withtheeluentindicated.InfraredspectrawererecordedonaPerkin-ElmerFT-IR1750.Ma
6、ssspectrawererecordedonaFinniganSSQ7000andHRMSonaFinniganMAT95,respectively.OpticalrotationsweremeasuredwithaPerkinElmerP241polarimeterina10cmcellwiththesolventindicated.ChiralHPLCanalysiswasperformedonaHewlett-Packard1050systemandChiracelOD,AD,or(S,S)-WhelkO-1colum
7、ns.26SupplementaryMaterial(ESI)forChemicalCommunicationsThisjournalis©TheRoyalSocietyofChemistry2002Diethylzincadditiontoaldehydes(generalprotocol)Theligand(0.005mmol,1mol%)wasweightintoa10mlvial,amagneticstirringbarwasaddedandthevialwasclosed.Thevialwasflushedwitha
8、rgontoluene(1mL)anddiethylzinc(1mL,1mmol,1Msolutioninhexane)wasaddedandthemixturewasstirredfor30min.atroomtemperature.Theresultingyellowso
