Organic Syntheses, Volume 90

David Hughes obtained his Ph.D. in physical organic chemistry under the direction of Professor Fred Bordwell at Northwestern University in 1981. After post-doctoral work in the laboratory of Professor Ned Arnett at Duke University, he joined the Process Research department of Merck Research Laboratories in 1982 and currently holds the position of Executive Director, Scientific Staff. His area of expertise is physical organic chemistry with a focus on elucidation of mechanisms of synthetically important organic reactions. In the mid-1990's, the Hughes group took on the challenge of developing a viable synthesis of a semi-synthetic pneumocandin antifungal candidate that was entering development at that time. This development candidate progressed through many hurdles and was ultimately approved under the trademark CANCIDAS in 2001. Along with his colleagues Robert Schwartz and Jim Balkovec, Dave was awarded the 2006 ACS Heroes of Chemistry Award for this work. Other Merck drugs that Dave has been instrumental in process design and development include Primaxin, Emend, and Cozaar. Dave has co-authored over 100 papers and has been a member of the editorial board for Organic Synthesis since 2008.

• Synthesis of Koser's Reagent and Derivatives Reagent for Divalent Sulfur Protection: Preparation of 4-Methylbenzenesulfonothioic Acid, S-[(1,1-Dimethylethyl)-Dimethylsilyl]oxy]methyl] EsterDiscussion Addendum for: Applications of (2S)-3-exo-Morpholinoisoborneol [MIB] in Organic SynthesisPreparation of (E)-N, N-Diethyl-2-styrylbenzamide by Rh-Catalyzed C-H ActivationEnantioselective Nitroaldol (Henry) Reaction of p-Nitrobenzaldehyde and Nitromethane Using a Copper (II) Complex Derived from (R, R)-1,2-Diaminocyclohexane: (1S)-1-(4-Nitrophenyl)-2-nitroethane-1-olSynthesis of N-Acetyl Enamides by Reductive Acetylation of Oximes Mediated with Iron(II) Acetate: N-(1-(4-Bromophenyl)vinyl)acetamideOxindole Synthesis via Palladium-catalyzed C-H FunctionalizationIntermolecular retro-Cope Type Hydroxylamination of Alkynes with NH2OH: E-1-(1-Hydroxycyclohexyl)ethanone oximePreparation of 1,5-Disubstituted 1,2,3-Triazoles via Ruthenium-catalyzed Azide Alkyne CycloadditionDiscussion Addendum for: Nickel-catalyzed Homoallylation of Aldehydes with 1,3-DienesEnantioselective Alkylation of N-(Diphenylmethylene)glycinate tert-Butyl Ester: Synthesis of (R)-2-(Benzhydrylidenamino)-3-Phenylpropanoic Acid tert-Butyl EsterEnantioselective Alkylation of 2-[(4-Chlorobenzyliden)Amino]Propanoic Acid tert-Butyl Ester: Synthesis of (R)-2-Amino-2-Methyl-3-Phenylpropanoic Acid tert-Butyl EsterPreparation of α-Fluorobis(phenylsulfonyl)methane (FBSM)Direct Conversion of Benzylic and Allylic Alcohols to Diethyl PhosphonatesSynthesis of 1-Naphthol via Oxidation of Potassium 1-NaphthyltrifluoroboratePotassium tert-Butoxide Mediated Synthesis of PhenanthridinonePreparation of N1-Phenylacetamidine 4-Bromobenzoate Using 2,2,2-Trichloroethyl Acetimidate HydrochloridePhenylacetamidine 4-Bromobenzoate Using 2,2,2-Trichloroethyl Acetimidate HydrochlorideDiscussion Addendum for: Stereoselective Synthesis of anti alpha-Methyl-beta-Methoxy Carboxylic CompoundsBimolecular Oxidative Amidation of Phenols: 1-(Acetylamino)-4-oxo-2,5-cyclohexadiene-1-acetic acid, Methyl EsterNickel-Catalyzed Cross-Coupling of Aryl Halides with Alkyl Halides: Ethyl 4-(4-(4-methylphenylsulfonamido)-phenyl)butanoateSynthesis of 1-Naphthol via Oxidation of Potassium 1-NaphthyltrifluoroboratePotassium tert-Butoxide Mediated Synthesis of PhenanthridinonePreparation of N1-Phenylacetamidine 4-Bromobenzoate Using 2,2,2-Trichloroethyl Acetimidate HydrochlorideDiscussion Addendum for: Stereoselective Synthesis of anti [alpha]-Methyl-[beta]-Methoxy Carboxylic CompoundsBimolecular Oxidative Amidation of Phenols: 1-(Acetylamino)-4-oxo-2,5-cyclohexadiene-1-acetic acid, Methyl EsterNickel-Catalyzed Cross-Coupling of Aryl Halides with Alkyl Halides: Ethyl 4-(4-(4-methylphenylsulfonamido)-phenyl)butanoateDiscussion Addendum for: Preparation of 4-Acetylamino-2, 2, 6, 6-tetramethylpiperidine-1-oxoammonium Tetrafluoroborate and the Oxidation of Geraniol to Geranial (2,6-Octadienal, 3,7-dimethyl-, (2e)- )Preparation of 3-Oxocyclohex-1-ene-1-carbonitrileAir Oxidation of Primary Alcohols Catalyzed by Copper(I)/TEMPO. Preparation of 2-Amino-5-bromo-benzaldehydeOne-Pot Preparation of Cyclic Amines from Amino AlcoholsPreparation of Tetrabutylammonium (4-fluorophenyl)trifluoroborateAllyl Cyanate-To-Isocyanate Rearrangement: Preparation of tert-Butyl 3,7-Dimethylocta-1,6-dien-3-ylcarbamatePalladium-Catalyzed Triazolopyridine Synthesis: Synthesis of 7-Chloro-3-(2-Chlorophenyl)-1,2,4-Triazolo[4,3-a]PyridinePreparation of DABSO from Karl-Fischer ReagentLow-epimerization Peptide Bond Formation with Oxyma Pure: Preparation of Z-L-Phg-Val-OMePractical Synthesis of Di-tert-Butyl-PhosphinoferrocenePreparation of 1-Benzyl-2-methyl-3-(ethoxycarbonyl)-4- (2-phenylethyl)-1H-pyrrole from 4-Phenyl-1,2-butadieneSynthesis of Highly Enantiomerically Enriched Amines by Asymmetric Transfer Hydrogenation of N-(tert-Butylsulfinyl)IminesSimplified Preparation of Dimethyldioxirane (DMDO)Practical and Efficient Synthesis of N-Formylbenzotriazole