Asymmetric Synthetic Methodology

David John Ager and Michael B. East

IntroductionNomenclatureWhy Asymmetric Synthesis?Methods to Achieve Asymmetric SynthesisResolutionA Question of ScaleGeneral RulesCarbonyl AdditionsHouk's RuleAllylic StrainBaldwin's RulesPericyclic Transition StatesOne-Carbon TransformationsInversions at a Single Carbon CenterChiral Organometallic ReagentsOther ReactionsReactions With Carbonyl CompoundsReactions of Carbonyl Compounds With NucleophilesAcetal ReactionsOther ElectrophilesOther ReactionsReductionsEnolate Reactions of Carbonyl CompoundsEnol Ethers and Enolate FormationReactions of Enol Ethers and EnolatesUse of Nitrogen DerivativesAsymmetric Deprotonations and ProtonationsReactions of Functionalized Carbonyl SystemsAlkylations of 1,2-Functionalized Carbonyl CompoundsReductions of 1,2-Functionalized Carbonyl CompoundsAlkylations of 1,3-Functionalized Carbonyl CompoundsReductions of 1,3-Functionalized Carbonyl CompoundsOther SystemsAldol and Related ReactionsThe Aldol Reaction: Methods of ControlThe Aldol Reaction: The Role of Enolate Geometry and Metal CounterionThe Formose ReactionPreparation and Reactions of AlkenesAlkene SynthesisReactions of AlkenesReactions of Functionalized AlkenesHydrogenationsOther Transition Metal Catalyzed ReactionsHydride Delivery AgentsReactions of Some Functionalized AlkenesConjugate AdditionsAllyl AlkylationsOther ReactionsAsymmetric Oxidations of Isolated AlkenesEpoxidationsReactions of Epoxides1,2-DiolsFormation and Reactions of Cyclic SulfatesPreparation and Reactions of AziridinesOxidations of Functionalized AlkenesEpoxidation of Allyl AlcoholsReactions of 2,3-Epoxy Alcohols and Related SystemsEpoxidations and Reactions of Other Unsaturated SystemsOther OxidationsOther SystemsPericyclic ReactionsThe Diels-Alder ReactionClaisen