Asymmetric Enamine Catalysis

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1、Chem.Rev.2007,107,5471-55695471AsymmetricEnamineCatalysisSantanuMukherjee,JungWoonYang,SebastianHoffmann,andBenjaminList*Max-Planck-Institutfu¨rKohlenforschung,D-45470Mu¨lheimanderRuhr,GermanyReceivedAugust28,2007Contents5.4.4.R-Iodination55605.5.R-Sulfenylation5560

2、1.Introduction54715.6.R-Selenylation55602.AsymmetricAldolReactions54736.OtherAsymmetricC-CBondFormingReactions55612.1.Introduction54736.1.IntramolecularR-AlkylationofAldehydes55612.2.IntramolecularAldolizations54746.2.AsymmetricR-AllylationofAldehydesand55612.2.1.En

3、olendoAldolizations5474Ketones2.2.2.EnolexoAldolizations54767.Asymmetricç-FunctionalizationofCarbonyl55612.3.IntermolecularAldolizations5477Compounds2.3.1.KetoneDonors54777.1.Introduction55612.3.2.AldehydeDonors54987.2.ç-AminationofR,â-UnsaturatedAldehydes55622.3.3.

4、DirectCatalyticAsymmetricsyn-Aldol55038.SummaryandOutlook:CurrentStatusand5562ReactionsFutureChallengesofAsymmetricEnamine3.AsymmetricMannichReactions5504Catalysis3.1.Introduction55049.Acknowledgments55643.2.DirectAsymmetricMannichReactionsof550410.References5565Ket

5、ones3.3.DirectAsymmetricMannichReactionsof5509Aldehydes1.Introduction3.4.IndirectAsymmetricMannichReactionsof5511PreformedAldimineswithKetonesThecatalysisbyprimaryandsecondaryaminesofelec-3.5.IndirectAsymmetricMannichReactionsof5514trophilicsubstitutionreactionsinth

6、eR-positionofcarbonylPreformedAldimineswithAldehydescompoundsandrelatedreactionsviaenamineintermediates3.6.IndirectAsymmetricMannichReactionsof5517iscalledenaminecatalysis.1,2ToalargedegreethischemistryPreformedAldimineswithR-Branchedcanbeconsideredthecatalyticvaria

7、ntoftheclassicalAldehydespreformedenaminechemistry(Scheme1)pioneeredby3.7.IndirectAsymmetricMannichReactionsof5518Stork.3-5Insuchtransformationsanenamine(III)isPreformedKetimineswithAldehydesgeneratedbyreactingacarbonylcompound(I)withanamine3.8.Asymmetricanti-Mannic

8、hReactions5518(II)underdehydrationconditions.Reactionoftheenamine3.9.ImmobilizedCatalystsforMannichReactions5521(III)canproceedviaanadditi