Organic Syntheses, Collective Volume 10

Jeremiah P. Freeman is the editor of Organic Syntheses, Collective Volume 10: A Revised Edition of Annual Volumes 75 - 79, published by Wiley.

• 7α-ACETOXY-(1Hβ, 6Hβ)-BICYCLO[4.4.1]UNDECA-2,4,8-TRIENE VIA CHROMIUMMEDIATED HIGHER ORDER CYCLOADDITION. STILLE COUPLINGS CATALYZED BY PALLADIUM-ON-CARBON WITH CUI AS A COCATALYST: SYNTHESIS OF 2-(4’-ACETYLPHENYL)THIOPHENE.ASYMMETRIC SYNTHESIS OF α-AMINO ACIDS BY THE ALKYLATION OF PSEUDOEPHEDRINE GLYCINAMIDE: L-ALLYLGLYCINE AND N-Boc-L-ALLYLGLYCINE.2-AMINO-3-FLUOROBENZOIC ACID.(1S,2R)-1-AMINOINDAN-2-OL.SYNTHESIS OF cis-4a(S),8a(R)-PERHYDRO-6(2H)-ISOQUINOLINONES FROM QUININE: 4a(S), 8a(R)-2-BENZOYLOCTAHYDRO-6(2H)-ISOQUINOLINONE.N-BENZYL-2,3-AZETIDINEDIONE.SULFINIMINES (THIOOXIMINE S-OXIDES): ASYMMETRIC SYNTHESIS OF METHYL (R)-(þ)-b-PHENYLALANATE FROM (S)-(þ)-N-(BENZYLIDENE)-p-TOLUENESULFINAMIDE.2-(N-BENZYL-N-MESITYLENESULFONYL)AMINO-1-PHENYL-1-PROPYL PROPIONATE.REGIOSELECTIVE MONOALKYLATION OF KETONES VIA THEIR MANGANESE ENOLATES: 2-BENZYL-6-METHYLCYCLOHEXANONE FROM 2-METHYLCYCLOHEXANONE.SYNTHESIS OF (-)-(E.S)-3-(BENZYLOXY)-1-BUTENYL PHENYL SULFONE VIA A HORNER-WADSWORTH- EMMONS REACTION OF (-)-(S)-2-(BENZYL OXY)PROPANAL.1-[N-BENZYLOXYCARBONYL-(1S)-1-AMINO-2-OXOETHYL]-4-METHYL-2,6,7-TRIOXABICYCLO[2.2.2]OCTANE.(3,4,5-TRIFLUOROPHENYL)BORONIC ACID-CATALYZED AMIDE FORMATION FROM CARBOXYLIC ACIDS AND AMINES: N-BENZYL-4-PHENYLBUTYRAMIDE.PHOTOCHEMICAL SYNTHESIS OF BICYCLO[1.1.1]PENTANE-1,3-DICARBOXYLIC ACID.BICYCLOPROPYLIDENE.RESOLUTION OF 1,1’-Bi-2-NAPHTHOL.(R,R)-N,N’-BIS(3,5-DI-tert-BUTYLSALICYLIDENE-1,2-CYCLOHEXANEDIAMINO MANGANESE(III) CHLORIDE, A HIGHLY ENANTIOSELECTIVE EPOXIDATION CATALYST.SYNTHESIS OF UNSYMMETRICAL BIARYLS USING A MODIFIED SUZUKI CROSSCOUPLING: 4-BIPHENYLCARBOXALDEHYDE.EFFICIENT SYNTHESIS OF HALOMETHYL-2,2’-BIPYRIDINES: 4,4’-BIS(CHLOROMETHYL)-2,2’-BIPYRIDINE.(R)-(+)- AND (S)-(–)-2,2’-BIS-(DIPHENYLPHOSPHINO)-1,1’-BINAPHTHYL (BINAP).BIS(PINACOLATO)DIBORON.PREPARATION OF BIS(2,4,6-TRIMETHYLPYRIDINE)IODINE(I) HEXAFLUOROPHOSPHATE AND BIS(2,4,6-TRIMETHYLPYRIDINE)BROMINE(I) HEXAFLUOROPHOSPHATE.3-(4-BROMOBENZOYL)PROPANOIC ACID.BROMOFLUORINATION OF ALKENES: 1-BROMO-2-FLUORO-2-PHENYLPROPANE.SYNTHESIS OF 4-(2-BROMO-2-PROPENYL)-4-METHYL-γ-BUTYROLACTONE BY THE REACTION OF ETHYL LEVULINATE WITH (2-BROMOALLYL) DIISOPROPOXYBORANE PREPARED BY HALOBORATION OF ALLENE.DIASTEREOSELECTIVE SYNTHESIS OF PROTECTED VICINAL AMINO ALCOHOLS: (S)-2-[(4S)-N-tert-BUTOXYCARBONYL-2,2-DIMETHYL-1,3-OXAZOLIDINYL]-2-tert-BUTYLDIMETHYLSILOXYETHANAL FROM A SERINE-DERIVED ALDEHYDE.BUTYL 4-CHLOROPHENYL SULFIDE.PHOTOINDUCED-ADDITION OF METHANOL TO (5S)-(5-O-tert-BUTYLDIMETHYLSILOXYMETHYL) FURAN-2(5H)-ONE: (4R,5S)-4-HYDROXYMETHYL-(5-O-tert-BUTYLDIMETHYLSILOXYMETHYL)FURAN-2(5H)-ONE.[3 + 4] ANNULATION USING A [β-(TRIMETHYLSILYL)ACRYLOYL]SILANE AND THE LITHIUM ENOLATE OF AN ?, ?-UNSATURATED METHYL KETONE: (1R*,6S*,7S*)-4-(tert-BUTYLDIMETHYLSILOXY)-6-(TRIMETHYLSILYL)BICYCLO[5.4.0]UNDEC-4-EN-2-ONE.(tert-BUTYLDIMETHYLSILYL)ALLENE.SYNTHESIS AND UTILIZATION OF INDIUM (I) IODIDE FOR IN SITU FORMATION OF ENANTIOENRICHED ALLENYLINDIUM REAGENTS AND THEIR ADDITION TO ALDEHYDES: (2R,3S,4S)-1-(tert-BUTYLDIPHENYLSILYLOXY)-2,4-DIMETHYL-5-HEXYN-3-OL.DIMETHYL SQUARATE AND ITS CONVERSION TO 3-ETHENYL-4-METHOXYCYCLOBUTENE-1,2-DIONE AND 2-BUTYL-6-ETHENYL-5-METHOXY-1,4-BENZOQUINONE.PREPARATION OF 1-BUTYL-3-METHYL IMIDAZOLIUM-BASED ROOM TEMPERATURE IONIC LIQUIDS.PREPARATION AND DIELS-ALDER REACTION OF A 2-AMIDO SUBSTITUTED FURAN: tert-BUTYL 3a-METHYL-5-OXO-2,3,3a,4,5,6-HEXAHYDROINDOLE-1-CARBOXYLATE.(S)-3-(tert-BUTYLOXYCARBONYLAMINO)-4-PHENYLBUTANOIC ACID.USE OF CERIUM(III) CHLORIDE IN THE REACTIONS OF CARBONYL COMPOUNDS WITH ORGANOLITHIUMS OR GRIGNARD REAGENTS FOR THE SUPPRESSION OF ABNORMAL REACTIONS: 1-BUTYL-1,2,3,4-TETRAHYDRO-1-NAPHTHOL.CAMPHORQUINONE AND CAMPHORQUINONE MONOXIME.PHOTO-INDUCED RING EXPANSION OF 1-TRIISOPROPYLSILYLOXY-1-AZIDOCYCLOHEXANE: PREPARATION OF e-CAPROLACTAM.3-CHLORO-2-(CHLOROMETHYL)-1-PROPENE.1-CHLORO-(2S,3S)-DIHYDROXYCYCLOHEXA-4,6-DIENE.6-CHLORO-1-HEXENE AND 8-CHLORO-1-OCTENE.2-CHLOROPHENYL PHOSPHORODICHLORIDOTHIOATE.3-CYCLOPENTENE-1-CARBOXYLIC ACID.CYCLOPROPENE: A NEW SIMPLE SYNTHESIS AND ITS DIELS-ALDER REACTION WITH CYCLOPENTADIENE.CYCLOPROPYLACETYLENE.EFFICIENT SYNTHESIS OF BROMIDES FROM CARBOXYLIC ACIDS CONTAINING A SENSITIVE FUNCTIONAL GROUP: DEC-9-ENYL BROMIDE FROM 10-UNDECENOIC ACID.TRIBUTYLSTANNANE (Bu3SnH)-CATALYZED BARTON-McCOMBIE DEOXYGENATION OF ALCOHOLS: 3-DEOXY-1,2:5,6-BIS-O-(1-METHYLETHYLIDENE)-?-D-ribo-HEXOFURANOSE.β-30,50-DI-O-BENZOYLTHYMIDINE.PREPARATION OF ENANTIOMERICALLY PURE α-N,N-DIBENZYLAMINOALDEHYDES: S-2-(N,N-DIBENZYLAMINO)-3-PHENYLPROPANAL.SYNTHESIS OF SYMMETRICAL trans-STILBENES BY A DOUBLE HECK REACTION OF (ARYLAZO)-AMINES WITH VINYLTRIETHOXYSILANE: trans-4,4'-DIBROMOSTILBENE.PREPARATION AND USE OF N,N'-DI-Boc-N"-TRIFLYLGUANIDINE.SYNTHESIS OF 8,8-DICYANOHEPTAFULVENE FROM CYCLOHEPTATRIENYLIUM TETRAFLUOROBORATE AND BROMOMALONONITRILE.DICYCLOHEXYLBORON TRIFLUOROMETHANESULFONATE.(R,R)-1,2:4,5-DIEPOXYPENTANE.ASYMMETRIC SYNTHESIS OF DIETHYL (R)-(-)-(1-AMINO-3-METHYLBUTYL)PHOSPHONATE.DIETHYL [(PHENYLSULFONYL)METHYL]PHOSPHONATE.6,7-DIHYDROCYCLOPENTA-1,3-DIOXIN-5(4H)-ONE.SYNTHESIS OF CHIRAL NON-RACEMIC DIOLS FROM (S,S)-1,2,3,4-DIEPOXYBUTANE: (2S,3S)-DIHYDROXY-1,4-DIPHENYLBUTANE.PREPARATION OF (E)-1-DIMETHYLAMINO-3-tert-BUTYLDIMETHYLSILOXY-1,3-BUTADIENE.(2S)-(–)-3-exo-(DIMETHYLAMINO)ISOBORNEOL [(2S)-(–)-DAIB].4-DIMETHYLAMINO-N-TRIPHENYLMETHYLPYRIDINIUM CHLORIDE.(R,R)- AND (S,S)-N,N0-DIMETHYL-1,2-DIPHENYLETHYLENE-1,2-DIAMINE.SYNTHESIS OF 1,1-DIMETHYLETHYL (S)-4-FORMYL-2,2-DIMETHYL-3-OXAZOLIDINECARBOXYLATE BY OXIDATION OF THE ALCOHOL.CONVERSION OF NITRILES INTO TERTIARY AMINES: N,N-DIMETHYLHOMOVERATRYLAMINE.NICKEL-CATALYZED COUPLING OF ARYL O-CARBAMATES WITH GRIGNARD REAGENTS: 2,7-DIMETHYLNAPHTHALENE.[4 + 3] CYCLOADDITION IN WATER: 2,4-endo,endo-DIMETHYL-8-OXABICYCLO[3.2.1]OCT-6-EN-3-ONE.SYNTHESIS OF β-LACTONES BY ALDOLIZATION OF KETONES WITH PHENYL ESTER ENOLATES: 3,3-DIMETHYL-1-OXASPIRO[3.5]NONAN-2-ONE.ANTI-SELECTIVE BORON-MEDIATED ASYMMETRIC ALDOL REACTION OF CARBOXYLIC ESTERS: (2S, 3R)-2,4-DIMETHYL-1,3-PENTANEDIOL.(4R,5R)-2,2-DIMETHYL-α,α,α',α'-TETRA(NAPHTH-2-YL)-1,3-DIOXOLANE-4,5-DIMETHANOL FROM DIMETHYL TARTRATE AND 2-NAPHTHYLMAGNESIUM BROMIDE.DIMETHYLTITANOCENE.9,10-DIPHENYLPHENANTHRENE.(R)-2-DIPHENYLPHOSPHINO-20-METHOXY-1,1’-BINAPHTHYL.5-PHENYLDIPYRROMETHANE AND 5,15-DIPHENYLPORPHYRIN.(4R,5S)-4,5-DIPHENYL-3-VINYL-2-OXAZOLIDINONE.1S-(–)-1,3-DITHIANE 1-OXIDE.ETHYL (R)-2-AZIDOPROPIONATE.ETHYL 5-CHLORO-3-PHENYLINDOLE-2-CARBOXYLATE.ETHYL 3-(p-CYANOPHENYL)PROPIONATE FROM ETHYL 3-IODOPROPIONATE AND p-CYANOPHENYLZINC BROMIDE.9-ETHYL-3,6-DIMETHYLCARBAZOLE (DMECZ)*.ETHYL GLYCIDATE FROM (S)-SERINE: ETHYL (R)-(+)-2,3-EPOXYPROPANOATE.(–)-2,4-O-ETHYLIDENE-D-ERYTHROSE AND ETHYL (E)-(–)-4,6-OETHYLIDENE-(4S,5R,1’R)-4,5,6-TRIHYDROXY-2-HEXENOATE.COPPER-CATALYZED CONJUGATE ADDITION OF FUNCTIONALIZED ORGANOZINC REAGENTS TO α, ?-UNSATURATED KETONES: ETHYL 5-(3-OXOCYCLOHEXYL)PENTANOATE.ULLMAN METHOXYLATION IN THE PRESENCE OF A 2,5-DIMETHYLPYRROLE-BLOCKED ANILINE: 2-FLUORO-4-METHOXYANILINE.PALLADIUM-CATALYZED AMINATION OF ARYL HALIDES AND ARYL TRIFLATES: N-HEXYL-2-METHYL-4-METHOXYANILINE AND N-METHYL-N-(4-CHLOROPHENYL)ANILINE.4-HYDROXY[1-13C]BENZOIC ACID.N-HYDROXY-4-(p-CHLOROPHENYL)THIAZOLE-2(3H)-THIONE.[4 + 2] CYCLOADDITION OF 1-DIMETHYLAMINO-3-tert-BUTYLDIMETHYLSILOXY-1,3-BUTADIENE WITH METHYL ACRYLATE: 4-HYDROXYMETHYL-2-CYCLOHEXEN-1-ONE.ASYMMETRIC SYNTHESIS OF (M)-2-HYDROXYMETHYL-1-(2-HYDROXY-4,6-DIMETHYLPHENYL)-NAPHTHALENE VIA A CONFIGURATIONALLY UNSTABLE BIARYL LACTONE.SYNTHESIS AND DIASTEREOSELECTIVE ALKYLATION OF PSEUDOEPHEDRINE AMIDES: (1S,2S)-PSEUDOEPHEDRINEPROPIONAMIDE AND [(1S,2S)-PSEUDOEPHEDRINE-(R)-2-METHYLHYDROCINNAMAMIDE.GENERATION AND USE OF LITHIUM PENTAFLUOROPROPEN-2-OLATE: 4-HYDROXY-1,1,1,3,3-PENTAFLUORO-2-HEXANONE HYDRATE.(R)-(+)-2-HYDROXY-1,2,2-TRIPHENYLETHYL ACETATE.2-(4-METHOXYPHENYL)-2-CYCLOHEXEN-1-ONE: PREPARATION OF 2-IODO-2-CYCLOHEXEN-1-ONE AND SUZUKI COUPLING WITH 4-METHOXYPHENYLBORONIC ACID.O4,O5-ISOPROPYLIDENE-1,2:3,6-DIANHYDRO-D-GLUCITOL FROM ISOSORBIDE.β-MERCAPTOPROPIONITRILE (2-CYANOETHANETHIOL).PREPARATION OF SECONDARY AMINES FROM PRIMARY AMINES VIA 2-NITROBENZENESULFONAMIDES: N-(4-METHOXYBENZYL)-3-PHENYLPROPYLAMINE.4-METHOXYCARBONYL-2-METHYL-1,3-OXAZOLE.SELECTIVE PROTECTION OF 1,3-DIOLS AT THE MORE HINDERED HYDROXY GROUP: 3-(METHOXYMETHOXY)-1-BUTANOL.(S,E)-1-(METHOXYMETHOXY)-1-TRIBUTYLSTANNYL-2-BUTENE.ACCELERATED SUZUKI COUPLING VIA A LIGANDLESS PALLADIUM CATALYST: 4-METHOXY-20-METHYLBIPHENYL.NUCLEOPHILIC AROMATIC SUBSTITUTION OF ARYL FLUORIDES BY SECONDARY NITRILES: 2-(2-METHOXYPHENYL)-2-METHYLPROPIONITRILE.TRANSFORMATION OF PSEUDOEPHEDRINE AMIDES INTO HIGHLY ENANTIOMERICALLY ENRICHED ALDEHYDES, ALCOHOLS, AND KETONES: (R)-α-METHYLBENZENEPROPANAL, (R)-β-METHYLBENZENEPROPANOL, AND (R)-2-METHYL-1-PHENYL-3-HEPTANONE.SYNTHESIS OF 4-, 5-, AND 6-METHYL-2,2’-BIPYRIDINE BY A NEGISHI CROSS-COUPLING STRATEGY: 5-METHYL-2,2’-BIPYRIDINE.(1’S,2’S)-METHYL-3O,4O-(1’,2’-DIMETHOXYCYCLOHEXANE-10,20 DIYL)-α-DMANNOPYRANOSIDE.FORMATION OF γ-KETO ESTERS FROM β-KETO ESTERS: METHYL 5,5-DIMETHYL-4-OXOHEXANOATE.SYNTHESIS OF CHIRAL (E)-CROTYLSILANES: [3R- AND 3S-]-(4E)-METHYL 3-(DIMETHYLPHENYLSILYL)-4-HEXENOATE.IN SITU CATALYTIC EPOXIDATION OF OLEFINS WITH TETRAHYDROTHIOPYRAN-4-ONE AND OXONE: trans-2-METHYL-2,3-DIPHENYLOXIRANE.ALLYLINDATION IN AQUEOUS MEDIA: METHYL 3-(HYDROXYMETHYL)-4-METHYL-2-METHYLENEPENTANOATE.SYNTHESIS OF AMINO ACID ESTER ISOCYANATES: METHYL (S)-2-ISOCYANATO-3-PHENYLPROPANOATE.REDUCTION OF SULFONYL HALIDES WITH ZINC POWDER: S-METHYL METHANETHIOSULFONATE.METHYL CARBAMATE FORMATION VIA MODIFIED HOFMANN REARRANGEMENT REACTIONS: METHYL N-(p-METHOXYPHENYL)CARBAMATE.METHYL 2,3-O-(6,6’-OCTAHYDRO-6,6’-BI-2H-PYRAN-2,2’-DIYL)-α-D-GALACTOPYRANOSIDE.[R-(R*,S*)]-β-METHYL-α-PHENYL-1-PYRROLIDINEETHANOL.METHYL (S)-2-PHTHALIMIDO-4-OXOBUTANOATE.THE SYNTHESIS OF 2-ALKYL-4-PYRONES FROM MELDRUM’S ACID: 2-METHYL-4HPYRAN-4-ONE.CATALYTIC ASYMMETRIC SYNTHESIS OF NITROALDOLS USING A LANTHANUM-LITHIUM-BINOL COMPLEX: (2S,3S)-2-NITRO-5-PHENYL-1,3-PENTANEDIOL.3-NITROPROPANAL, 3-NITROPROPANOL, AND 3-NITROPROPANAL DIMETHYL ACETAL.[4 + 3] CYCLOADDITION OF AMINOALLYL CATIONS WITH 1,3-DIENES: 11-OXATRICYCLO-[4.3.1.12,5]UNDEC-3-EN-10-ONE.2-(3-OXOBUTYL)CYCLOPENTANONE-2-CARBOXYLIC ACID ETHYL ESTER.1-OXO-2-CYCLOHEXENYL-2-CARBONITRILE.PENTA-1,2-DIEN-4-ONE (ACETYLALLENE).ISOMERIZATION OF β-ALKYNYL ALLYLIC ALCOHOLS TO FURANS CATALYZED BY SILVER NITRATE ON SILICA GEL: 2-PENTYL-3-METHYL-5-HEPTYLFURAN.(+)-(1S,2R)- AND (–)-(1R,2S)-trans-2-PHENYLCYCLOHEXANOL VIA SHARPLESS ASYMMETRIC DIHYDROXYLATION (AD).(R)-3-PHENYLCYCLOHEXANONE.(2S,3S)-(+)-(3-PHENYLCYCLOPROPYL)METHANOL.MOLYBDENUM CARBONYL-CATALYZED ALKYNOL CYCLOISOMERIZATION: 2-PHENYL-2,3-DIHYDROFURAN.GENERATION OF 1-PROPYNYLLITHIUM FROM (Z/E)-1-BROMO-1-PROPENE: 6-PHENYLHEX-2-YN-5-EN-4-OL.CATALYTIC ASYMMETRIC ALLYLATION REACTIONS: (S)-1-PHENYLMETHOXY)-4-PENTEN-2-OL.CATALYTIC ENANTIOSELECTIVE ADDITION OF DIALKYLZINCS TO ALDEHYDES USING (2S)-(–)-3-exo-(DIMETHYLAMINO)ISOBORNEOL [(2S)-DAIB]: (S)-1-PHENYL-1-PROPANOL.MONO-C-METHYLATION OF ARYLACETONITRILES AND METHYL ARYLACETATES BY DIMETHYL CARBONATE: A GENERAL METHOD FOR THE SYNTHESIS OF PURE 2-ARYLPROPIONIC ACIDS. 2-PHENYLPROPIONIC ACID.PREPARATION OF CYANOALKYNES: 3-PHENYL-2-PROPYNENITRILE.N-VINYLPYRROLIDIN-2-ONE AS A 3-AMINOPROPYL CARBANION EQUIVALENT IN THE SYNTHESIS OF SUBSTITUTED 1-PYRROLINES: 2-PHENYL-1-PYRROLINE.(PHENYL)[2-(TRIMETHYLSILYL)PHENYL]IODONIUM TRIFLATE, AN EFFICIENT AND MILD BENZYNE PRECURSOR: PREPARATION OF 1,4-DIHYDRONAPHTHALENE 1,4-OXIDE.[1.1.1]PROPELLANE.1,2-METALLATE REARRANGEMENT: (Z)-4-(2-PROPENYL)-3-OCTEN-1-OL.1,4,7,10-TETRAAZACYCLODODECANE.(+)-(1R,2S,3R)-TETRACARBONYL[(1-3Z)-1-(PHENYLSULFONYL)-BUT-2-EN-1-YL]IRON(1+) TETRAFLUOROBORATE.USE OF 1,2,4,5-TETRABROMOBENZENE AS A 1,4-BENZADIYNE EQUIVALENT: anti- AND syn-1,4,5,8-TETRAHYDROANTHRACENE 1,4:5,8-DIEPOXIDES.INDOLE SYNTHESIS BY Pd-CATALYZED ANNULATION OF KETONES WITH o-IODOANILINE: 1,2,3,4-TETRAHYDROCARBAZOLE.6A-O-p-TOLUENESULFONYL-β-CYCLODEXTRIN.6A-O-p-TOLUENESULFONYL-β-CYCLODEXTRIN.α-TOSYLBENZYL ISOCYANIDE.THE DESS-MARTIN PERIODINANE: 1,1,1-TRIACETOXY-1,1-DIHYDRO-1,2-BENZIODOXOL-3-(1H)-ONE.WITTIG OLEFINATION OF PERFLUOROALKYL CARBOXYLIC ESTERS; SYNTHESIS OF 1,1,1-TRIFLUORO-2-ETHOXY-5-PHENYLPENT-2-ENE AND 1-PERFLUOROALKYL EPOXY ETHERS: 1,1,1-TRIFLUORO-2-ETHOXY-2,3-EPOXY-5-PHENYLPENTANE.2-TRIMETHYLSILYLETHANESULFONYL CHLORIDE (SES-CI).TRIS(2-PERFLUOROHEXYLETHYL)TIN HYDRIDE: A HIGHLY FLUORINATED TIN HYDRIDE WITH ADVANTAGEOUS FEATURES OF EASY PURIFICATION.VITAMIN D2 FROM ERGOSTEROL.TYPE OF REACTION INDEX.TYPE OF COMPOUND INDEX.FORMULA INDEX.AUTHOR INDEX.GENERAL INDEX.HAZARD AND WASTE DISPOSAL INDEX.CONCORDANCE INDEX.