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Chem 51

A. Ersin ACAR
2011 Spring Semester
Course Content:

A) Modification of functional groups
1. Reduction

1. Heterogeneous catalysis 2. Homogeneous catalysis 3. Hydrogenation of C=C by diimide 4. Asymetric hydrogenation of acids (esters)-acylaminoacrylics 1.2. Hydrogenolysis of C-O, C-S, C-X, N-O, O-O bonds 1. H2/Pd (Pt, Ni) 2. Hydrogenolysis of C-Het at α position of C=O 1. Reduction of aromatic compounds: Birch reduction 2. Reduction of dienes and conjugated enones 3. Reduction of acetylenes 4. Reduction of phosphates 1. Meerwin-Pondorff reaction 2. Metalic Hydrides - Sodium borohydride - Lithium triethyl borohydride - Lithium tri-sec butyl borohydride - Sodium cyanoboprohydride - Diborane - Lithium aluminum hydride - Lithum aliminum tris (t-butoxy) hydride - Aluminum hydride - Diisobutyl aluminum hydride - Asymetric reduction of carbonyl compounds catalyzed by 1.5. Reduction of carbonyls to CH2 or CH=C 1. Clemmensen reduction 2. Wolff-Kishner reduction - Modification by Huang-Minlon - Modification by Caglioti 3. Desulfurization of thioacetals 4. Bamford-Stevens-Shapiro reaction 2. Oxidation

1. Oxidation of alcohols to carbonyl compounds - Common reagents: Cr (VI) - Collins reagent - PCC - Pfitzner-Moffat and Swern Oxidations - Kornblum oxidation - MnO2 oxidation 3. Photolysis 4. Oxidation of enolates 5. Wacker oxidation 1. Bishydroxylation of olefins (OsO4) 2. Epoxidation of olefins - By peracids - Sharpless asymetric epoxidation - Reactions of epoxides (opening, rearengement, eliminations) 3. Bromohydrines 4. Iodolactonization 5. Oxymercuration 6. Hydroboration 1. Ozonolysis 2. Cleavage of 1,2-diols 3. Baeyer-Villiger oxidation 2.4. photooxidation of olefins by singlet oxygen 1. Reaction with 1,3-dienes 2. Reaction with isolated double bonds containing an allylic hydrogen 3. Reaction with enolic ethers and enamines 3. Formation of C-heteroatom bonds
- Nucleophilic substitution - Mitsunobu reaction 1. Syntheses of amines by nitrogen containing nucleophiles 2. Amination of enolate electrophiles 3. Rearrangements (cleavage of one C-C bond) - Beckmann rearrangement - Curtius rearragement
4. Elimination reactions
1. Pyrolysis of carboxylic esters 2. Chugaev elimination 3. Cope elimination 4. Elimination of sulfoxydes, selenoxydes 5. Elimination of epoxydes 4.4. Reductive elimination 4.5. Oxydative elimination 4.6. Cycloreversions 1. Winter-Corey reaction 2. Deprotonation of benzaldehyde-acetals 3. Ramberg-Bäcklund reaction B) C-C Bond Formation
1. Polar reactions
1.1. Organolithium and Grignard reagents as nucleophiles - Metalation of halogenated compounds - Hydrogen/metal exchange - Halogen/metal exchange - General reactivity of electrophiles - Reaction of Organolithium and Grignard reagents - Diastereoselectivity of nucleophilic addition (Felkin-Anh, Cram - Enantioselectivity of organozinc/aldehyde additions 1.2. Reaction with organocopper reagents 1. Dithianes 2. O-Alkylated cyanohydranes 3. Alpha lithiated vinyl ethers 1.4. Homoenolate equivalents 1.5. Olefination of carbonyl compounds 1. Wittig reaction (Unstabilized ylides) 2. Horner-Emmons modification (stabilized ylides) 3. C.W. Still Modification 4. Peterson reaction 5. Methylenation of carbonyl compounds by Tebbe reagent 1. Reaction with saturated aldehydes and ketones 2. Reaction with α, β-unsaturated ketones 1. Preparation of enolates by α-deprotonation 2. Alkylation - Alkylation of enolates derived from 1,3-dicarbonyl compounds - Alkylation at γ position of 1,3-dicarbonyl compounds - Alkylation of monocarbonyl compounds - Formation of enolates in a regiocontrolled manner - Control of E/Z configuration – Ireland Model - Enantioselective alkylation of enolates with chiral auxiliaries 3. Preparation of enolates by other methods - Reduction of conjugated enones - Conjugated addition (1,4) of organocopper compounds - Reduction of α-heterosubstituted ketones - Cleavage of vinyloxysilanes - Robinson annulation - Silylvinylketones as Michael receptors - Cross condensation - Stabilization of aldol adduct by chelation - Lithiated imines as enolate analogues - Silyloxyvinyl derivatives (Silylether enolates-Mukaiyama) - Vinyloxyboranes (Evans, Masamune) - Asymetric Aldol condensation (syn or anti selective) 1. Preparation 2. Alkylation of –N and –C 3. Michael reaction 4. Acylation 1. Reaction of enols with iminium salts 2. N-Acyl-iminium salts (Speckamp) 1.10. Acylation of aromatic and olefinic compounds 1.11. Vinyl- and allyl-silanes as nucleophiles 2. Pericyclic reactions,
- Regiochemistry of the addition - Stereochemistry of the addition - Diels-Alder cycloreversion (retro) - Catalysis by Lewis Acids - π-facial selectivity 3. [2+2] Cycloadditions 4. [1+2] cycoadditions 2.2. Chelotropic reactions 2.3. Electrocyclic reactions 1. Cyclobutene-1,3dienes 2. Nazarov eraction - Inter- and intramolecular - Mg-ene reaction (Mg transfer) 1. [1,2] rearrangement 2. [2,3] migration 3. [3,3] rearrangement - Cope rearrangement - Anionic Oxy-Cope rearrangement - Claisen-Cope Rearrangement
3. Radical reactions
3.1. Cyclization 3.2. Cyclization by halogen atom transfer 1. Mechanism, limitations 2. De-Mayo reactions 3. Intramolecular reactions 4. Reaction catalyzed by Pd complexes
4.1. Pd catalyst 4.2. Fundamental reactions 1. Oxydative addition, reductive elimination 2. Insertion 3. β-Elimination 4. π-allyl complexes of Palladium as electrophiles Recommended references: (all available in the library)

W. Carruthers (3rd, 4th editions) ‘Some Modern Methods of Organic Synthesis’,
Cambridge University Press 1986 (3rd), 2004 (4th).
Herbert O. House ‘Modern Synthetic Reactions’
Carrey and Sundberg ‘Advanced Organic Chemistry Part B: Reactions and Synthesis’
Plenum Press.
Journals: JORG, JACS, Synthesis, etc.
Websites for name reactions: (Many others exist)


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