Organic Syntheses, Volume 93

ISBN-13: 9781119349020 / Angielski / Twarda / 2017 / 464 str.

Charles K. Zercher

Opis

The current volume continues the tradition of the Organic Syntheses series, providing carefully checked and edited experimental procedures that describe important synthetic methods, transformations, reagents, and synthetic building blocks or intermediates with demonstrated utility in organic synthesis. These significant and interesting procedures should prove worthwhile to many synthetic chemists working in increasingly diverse areas. A trusted guide for professionals in organic and medicinal chemistry in academia, government, and industries, including pharmaceuticals, fine chemicals, agrochemicals, and biotechnological products.

Spis treści

DIBALH–Mediated Reductive Ring–Expansion Reaction of Cyclic Ketoxime 1

Preparation of 2–(2–(Dicyclohexylphosphino)phenyl)–1–methyl 1H–indole (CM–phos)

Synthesis of 5–(Hydroxymethyl)furfural (HMF) 29

Erratum for: Titanium–Mediated Addition of Silyl Dienol Ethers to Electrophilic Glycine: 4–Ketopipecolic Acid Hydrochloride 37

Nickel–Catalyzed Synthesis of Ketones from Alkyl Halides and Acid Chlorides: Preparation of Ethyl 4–Oxododecanoate 50

Trichloroboron–promoted Deprotection of Phenolic Benzyl EtherUsingPentamethylbenzene as a Non Lewis–Basic Cation Scavenger 63

Enantioselective Synthesis of , –Disubstituted Lactones via a Chiral Brønsted Acid–Catalyzed Intramolecular Cyclization 75

Enantioselective Synthesis of –Bromonitroalkanes for Umpolung Amide Synthesis: Preparation of tert–Butyl
((1R)–1–(4–(benzyloxy)phenyl)–2–bromo–2–nitroethyl)carbamate 88

Synthesis of 1–Bromopyrene and 1–Pyrenecarbaldehyde 100

Intermolecular [2+2] Cycloaddition of Alkynes with Alkenes Catalyzed by Gold(I) 115

Photochemical Benzannulation of N–Phosphoryl Ynamides and –Diazo Ketones in Continuous Flow 127

Trifluoromethylation of Aryl Iodides Catalyzed by the Copper(I)–Phen Complex 147

Copper–catalyzed Cyanation of Alkenyl Iodides 163

Visible Light Photocatalysis of Radical Cation Diels Alder Cycloadditions: Preparation of Tris(2,2 –bipyrazyl) Ruthenium(II) Bis(tetrakis(3,5–bis(trifluoromethyl)phenyl)borate) 178

Preparation of Methyl 1,2,3,4–tetra–O–acetyl– –D–glucopyranuronate 200

Preparation of 1,5–Dioxaspiro[5.5]undecan–3–one 210

Oxyboration: Synthesis of Borylated Benzofurans 228

Synthesis of 1–Iodopropyne 245

Potassium tert–Butoxide Catalyzed Dehydrogenative Cross–Coupling of Heteroarenes with Hydrosilanes 263

Synthesis of –Carboline 272

Synthesis of Methyl 1–Formylcyclopropanecarboxylate utilizing Ti–Claisen Condensation 286

Nickel–Catalyzed Suzuki Miyaura Coupling in t–Amyl Alcohol for the Preparation of 5–(Furan–3–yl)pyrimidine 306

Preparation of (S)–Nonafluorobutanesulfinamide 319

Preparation of 1–Methylimidazole–N–oxide (NMI–O) 331

Palladium–Catalyzed Direct Amination of Allylic Alcohols at Room Temperature 341

Preparation of 1,1–Difluoroallenes by Difluorovinylidenation of Carbonyl Compounds 352

Rhodium–Catalyzed Addition of Carboxylic Acids to Terminal Alkynes towards Z–Enol Esters 367

Copper–Catalyzed Semi–Reduction of Alkynes 385

Synthesis of Cyclobutanes by Lewis Acid–Promoted Ketene–Alkene [2+2] Cycloadditions 401

Synthesis of 2,2–Dichloroimidazolidine–4,5–diones and their Application in Chlorodehydroxylation 413

O autorze

Huw M. L. Davies, PhD, joined the Emory University faculty in 2008 as the Asa Griggs Candler Professor of Organic Chemistry. Prior to Emory, he held the positions of UB Distinguished Professor and Larkin Professor of Organic Chemistry at the University at Buffalo, the State University of New York. Dr. Davies received his BSc degree from University College in Cardiff, Wales and his PhD from the University of East Anglia. He completed his post–doctoral training at Princeton University.