有机合成化学第二章.pdfVIP

SyntheticOrganicChemistry

合成化学

Lecture02EnolateChemistry:Aldol

andRelatedReactions

Dr.ShouyunYu

俞寿云副教授

1

ReadingAssignment

Trost,B.M.;Brindle,C.S.Chem.Soc.Rev.2010,39,1600.

Geary,L.M.;Hultin,P.G.TetrahedronAsymm.2009,20,131.

Guillena,G.;Najera,C.;Ramon,D.J.TetrahedronAsymm.2007,18,2249.

Schetter,B.;Mahrwald,R.Angew.Chem.Int.Ed.2006,45,7506.

Cordova,Aetal,Chem.Eur.J.2006,12,5383.

Palomo,C.;Oiarbide,M.;Garcia,J.M.Chem.Soc.Rev.2004,33,65.

Notz,W.;Tanaka,F.;Barbas,C.F.Acc.Chem.Res.2004,37,580.

Mahrwald,R.Curr.Org.Chem.2003,7,1713.

Alcaide,B.;Almendros,P.Eur.J.Org.Chem.2002,1595.

Machajewski,T.D.;Wong,C.H.Angew.Chem.Int.Ed.2000,39,1352.

Johnson,J.S.;Evans,D.A.Acc.Chem.Res.2000,33,325.

Denmark,S.E.;Stavenger,R.A.Acc.Chem.Res.2000,33,432.

2

ClassificationofOrganicReactions

■Ionic

Ionsorelectronsmovinginpairs

■Pericyclic

Cyclictransitionstructures

Concertedbondforming/breaking(notalwayssynchronous)

Singlestepwithnointermediate

■Radical

Correlatedmovementofsingleelectrons

3

IonicOrganicReactions

4

ReactionwithCarbonylGroup

Nucleophilicadditionofaldehydesorketones

NucleophilesReactions

HydrideReduction

Organometallicspecies1,2-addition

EnolatesAldol

Electron-deficientalkene