Chapter 5Reduction of Carbon-CarbonMultiple Bonds, CarbonylGroups, and Other FunctionalGroupsIntroduction5.1. Addition of Hydrogen at Carbon-Carbon Multiple Bonds5.1.1. Hydrogenation Using Heterogeneous Catalysts5.1.1. Hydrogenation Using Heterogeneous Catalysts5.1.1. Hydrogenation Using Heterogeneous Catalysts5.1.2. Hydrogenation Using Homogeneous CatalystsCrabtree catalystCrabtree catalyst5.1.3. Enantioselective Hydrogenation215.1.3. Enantioselective HydrogenationLigands:Shen Li, Shou-Fei Zhu, Can-Ming Zhang, Song Song, and Qi-Lin ZhouJ. Am. Chem. Soc., 2008, 130 (27), 8584-8585Prof. Qi-Lin Zhou, State Key Laboratory of Elemento-Organic ChemistryMechanism5.1.5. Hydrogen Transfer from Diimide5.2. Catalytic Hydrogenation of Carbonyl and Other Functional Groups5.2. Catalytic Hydrogenation of Carbonyl and Other Functional Groups5.2. Catalytic Hydrogenation of Carbonyl and Other Functional Groups5.3. Group III Hydride-Donor Reagents5.3.1. Comparative Reactivity of Common Hydride Donor Reagents5.3.1. Comparative Reactivity of Common Hydride Donor Reagents5.3.1. Comparative Reactivity of Common Hydride Donor Reagents5.3.1.1. Partial Reduction of Carboxylic Acid Derivatives-forming aldehyde5.3.1.2. Reduction of Imines and Amides to Amines.5.3.1.3. Reduction of ,-Unsaturated Carbonyl Compounds5.3.2. Stereoselectivity of Hydride ReductionThe NaBH4-CeCl3 reagent is different, it has been observed to give hydride delivery from the more hindered face of certain bicyclic ketones5.3.2. Stereoselectivity of Hydride Reduction-attack from the less hinded face.5.3.2. Stereoselectivity of Hydride Reduction5.3.2.3. Chela-tion Control.5.3.2.3. Chelation Control.5.3.2.3. Chelation Control.5.3.2.3. Chelation Control.5.3.2.3. Chelation Control.5.3.3. Enantioselective Reduction of Carbonyl Compounds5.3.3.1. Reduction with Chiral Boranes5.3.2.3. Chelation Control.