Organic Syntheses, Collective Volume 10: A Revised Edition of Annual Volumes 75 – 79

Compiles all procedures outlined in Organic Syntheses Volumes 75–79
Organic Syntheses consists of protocols for the synthesis of useful chemical compounds. Each protocol is repeated in the laboratory of one of the editorial board members for accuracy or for missing experimental details prior to publication. For each protocol, safety warnings are presented along with detailed experimental descriptions for the preparation, purification, and identification of the compound. Additionally, special reaction conditions are detailed, along with the source of reagents, waste disposal information, a discussion of the results, references to the primary literature, and an appendix of nomenclature and registry numbers. Continuing the tradition of providing significant and interesting procedures, Organic Syntheses, Collective Volume X is a compilation of revised editions of Annual Volumes 75 through 79. Following precedent, there is no specific or central theme to this volume, but the procedures can be organized into four main categories: (1) asymmetric syntheses, chiral auxiliaries, and chiral ligands; (2) reactions that are promoted by metals or proceed via organometallic intermediates; (3) cycloaddition reactions; (4) valuable synthetic transformations and building blocks.

Spis treści:
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)–ISOQUINOL INONES 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–TRIMETHYLPYRI DINE)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 I ONIC 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