Chapter

5Reduction

of

Carbon-CarbonMultiple

Bonds,

CarbonylGroups,

and

Other

FunctionalGroupsNov.

20th,20085.2.

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

GroupsGroup

IIIHydride-Donor

ReagentsComparative

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

hydridedelivery

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.ChelationControl.5.3.2.3.ChelationControl.5.3.2.3.ChelationControl.EnantioselectiveReductionofCarbonylCompoundsReductionwithChiralBoranes5.3.2.3.ChelationControl.5.3.4.ReductionofOtherFunctionalGroupsbyHydrideDRoneod疫ruscti揉ono薯fh哨a淘li撈deMechanism-radicalDonorsEpoxideopenning:lesshinderedcarbonandaxialapproachbythenucleophile.5.3.4.ReductionofOtherFunctionalGroupsbyHydrideReductionofhalide丙ctionsInvolvingSiliconHydrides5.4.GroupIVHydrideDonors5.4.1.Rea1.2.3.4.Reductivecondensationofsilyletherswithcarbonylcompo豪undstoformethers,usesTMSOTfasthecatalystMechanism123Copper-catalyzedsystems5.4.2.HydrideTransferfromCarbon5.5.ReductionReactionsInvolvingHydrogenAtomDonTheorderofreactivityforthehalidesisRI>RBr>RCl>RF,whihreflectstherelativeeaseofthehalogenatomabstraction5.5.ReductionReactionsInvolvingHydrogenAtomDon5.5.ReductionReactionsInvolvingHydrogenAtomDon5.6.Dissolving-MetalReductions5.6.1.AdditionofHydrogen5.6.1s.1.ReductionofKetonesandEnone5.6.1.2.Dissolving-MetalReduct巡壽ionofAromaticCompoundBirchReduction5.6.2.ReductiveRemovalofFunctionalGroups125.6.2.ReductiveRemovalofFunctionalGroups35.6.2.ReductiveRemovalofFunctionalGroups5.6.2.ReductiveRemovalofFunctionalGroups5.6.2.ReductiveRemovalofFunctionalGroups5.7.1.ReductiveDeoxygenationofCarbonylGroupstoM5.7.2.ReductionofCarbonylCompoundstoAlkenes5.8.ReductiveEliminationandFragmentationChapter6.ConcertedCycloadditions,UnimolecularRearrangements,andThermalEliminationsNov.20th,2008Diels-AlderReactionsTheDiels-AlderReaction:GeneralFeatures6.1.2.SubstituentEffectsontheDiels-AlderReaction6.1.2.SubstituentEffectsontheDiels-AlderReaction6.1.2.SubstituentEffectsontheDiels-AlderReaction6.1.2.SubstituentEffectsontheDiels-AlderReaction6.1.2.SubstituentEffectsontheDie