90-63-1

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 95, p. 2694, 1973 DOI: 10.1021/ja00789a053Synthetic Communications, 22, p. 1523, 1992 DOI: 10.1080/00397919208021623

InChI:InChI=1/C9H10O2/c1-7(10)9(11)8-5-3-2-4-6-8/h2-6,9,11H,1H3

Upstream product

• 917-64-6 methyl magnesium iodide 
• 4410-31-5 (RS)-mandelamide 
• 4304-93-2 2-methyl-1-methoxy-1-phenyl-oxirane 
• 623-11-0 1-methyl-4-nitrosobenzene 
• 135762-75-3 5-phenyl-5-hydroxy-2,4-pentanedione 
• 23022-83-5 1-bromo-1-phenyl-2-propanone 
• 19275-80-0 1-acetoxy-1-phenyl-acetone 
• 5650-40-8 2-hydroxypropiophenone 
• 532-28-5 (RS)-mandelonitrile 
• 5650-44-2 methcathinone 
• 64-19-7 acetic acid 
• 611-71-2 MANDELIC ACID 
• 119-51-7 1-phenyl-1,2-propanedione 2-oxime 
• 4187-87-5 1-Phenyl-2-propyn-1-ol 

Downstream Products

• 5703-17-3 1-phenyl-2-piperidin-1-yl-propan-1-one 
• 101596-63-8 2-methyl-1,4-diphenyl-3-butyne-1,2-diol 
• 93015-37-3 2-methyl-1,3-diphenyl-propane-1,2-diol 
• 26226-58-4 1-Hydroxy-1-phenyl-2-propanone oxime 
• 7624-52-4 (+/-)-1-hydroxy-1-phenyl-acetone semicarbazone 
• 102872-97-9 1-hydroxy-1-phenyl-acetone thiosemicarbazone 
• 20907-13-5 2-methyl-1-phenylpropane-1,2-diol 
• 90925-49-8 2-phenyl-2,3-butanediol 
• 1084-78-2 (1RS,2RS)-(+/-)-1,2-diphenyl-1,2-propandiol 
• 41728-16-9 1,2-diphenylpropan-1,2-diol 
• 40421-52-1 (1RS,2SR)-1-phenylpropane-1,2-diol 
• 20999-77-3 1-phenyl-propane-1,2-dione-2-phenylhydrazone 
• 90-81-3 ephedrine 
• 7624-24-0 1-methoxy-1-phenyl-acetone 

Relevant academic research and scientific papers

g-C3N4/metal halide perovskite composites as photocatalysts for singlet oxygen generation processes for the preparation of various oxidized synthons

g-C3N4/metal halide perovskite composites were prepared and used for the first time as photocatalysts forin situ1O2generation to perform hetero Diels-Alder, ene and oxidation reactions with suitable dienes and alkenes. The standardized methodology was made applicable to a variety of olefinic substrates. The scope of the method is finely illustrated and the reactions afforded desymmetrized hydroxy-ketone derivatives, unsaturated ketones and epoxides. Some limitations were also observed, especially in the case of the alkene oxidations, and poor chemoselectivity was somewhere observed in this work which is the first application of MHP-based composites forin situ1O2generation. The experimental protocol can be used as a platform to further expand the knowledge and applicability of MHPs to organic reactions, since perovskites offer a rich variety of tuning strategies which may be explored to improve reaction yields and selectivities.

Zinc salt-catalyzed reduction of α-aryl imino esters, diketones and phenylacetylenes with water as hydrogen source

The zinc salt-catalyzed reduction of α-aryl imino esters, diketones and phenylacetylenes with water as hydrogen source and zinc as reductant was successfully conducted. The presented method provides a low-cost, environmentally friendly and practical preparation of α-aryl amino esters, α-hydroxyketones and phenylethylenes. By using D2O as deuterium source, the corresponding products were obtained in high efficiency with excellent deuterium incorporation rate, which gives a cheap and safe tool for access to valuable deuterium-labelled compounds. This journal is

Whole-Cell Biocatalysis in Seawater: New Halotolerant Yeast Strains for the Regio- and Stereoselectivity Reduction of 1-Phenylpropane-1,2-Dione in Saline-Rich Media

The application of green chemistry concepts in catalysis has considerably increased in recent years, and the interest in using sustainable solvents in the chemical industry is growing. One of the recent proposals to fall in line with this is to employ seawater as a solvent in biocatalytic processes. This involves selecting halotolerant strains capable of carrying out chemical conversions in the presence of the salt concentrations found in this solution. Recent studies by our group have revealed the interest in using strains belonging to Debaryomyces and Schwanniomyces for catalytic processes run in this medium. In the present work, we select other yeasts based on their halotolerance to widen the scope of this strategy. We consider them for the monoreduction of 1-phenylpropane-1,2-dione, a well-characterized reaction that produces acyloin intermediates of pharmaceutical interest. The results obtained herein indicate that using seawater as a solvent for this reaction is possible. The best ones were obtained for Saccharomyces cerevisiae FY86 and Kluyveromyces marxianus, for which acyloins with different stereochemistry were obtained with good to excellent enantiomeric excess.

Iron-catalyzed regiodivergent alkyne hydrosilylation

Although tremendous effort has been devoted to the development of methods for iron catalysis, few of the catalysts reported to date exhibit clear superiority to other metal catalysts, and the mechanisms of most iron catalysis remain unclear. Herein, we report that iron complexes bearing 2,9-diaryl-1,10-phenanthroline ligands exhibit not only unprecedented catalytic activity but also unusual ligand-controlled divergent regioselectivity in hydrosilylation reactions of various alkynes. The hydrosilylation protocol described herein provides a highly efficient method for preparing useful di- and trisubstituted olefins on a relatively large scale under mild conditions, and its use markedly improved the synthetic efficiency of a number of bioactive compounds. Mechanistic studies based on control experiments and density functional theory calculations were performed to understand the catalytic pathway and the observed regioselectivity.

Regio- and stereoselective multi-enzymatic aminohydroxylation of β-methylstyrene using dioxygen, ammonia and formate

We report an enzymatic route for the formal regio- and stereoselective aminohydroxylation of β-methylstyrene that consumes only dioxygen, ammonia and formate; carbonate is the by-product. The biocascade entails highly selective epoxidation, hydrolysis and hydrogen-borrowing alcohol amination. Thus, β-methylstyrene was converted into 1R,2R and 1S,2R-phenylpropanolamine in 59-63% isolated yields, and up to >99.5 : 0.5 dr and er.

Sequential Reduction of Nitroalkanes Mediated by CS2 and Amidine/Guanidine Bases: A Controllable Nef Reaction

In this letter, we describe a mild, functional group-tolerant reductive Nef reaction that utilizes CS2 and an amidine or guanidine base to sequentially cleave N-O bonds. These conditions transform secondary nitroalkanes to ketones via an isolable oxime with minimal erosion at labile stereogenic carbons, show excellent compatibility with groups sensitive to oxidizing or reducing conditions, display good scalability, and are well-suited for generating useful 3-pyrrolidinone motifs from readily accessible 1,3-dipolar cycloaddition products.

Homogeneous Palladium-Catalyzed Transfer Hydrogenolysis of Benzylic Alcohols Using Formic Acid as Reductant

We report the first homogeneous palladium-based transfer hydrogenolysis of benzylic alcohols using an in situ formed palladium-phosphine complex and formic acid as reducing agent. The reaction requires a catalyst loading as low as only 1 mol % of palladium and just a slight excess of reductant to obtain the deoxygenated alkylarenes in good to excellent yields. Besides demonstrating the broad applicability for primary, secondary and tertiary benzylic alcohols, a reaction intermediate could be identified. Additionally, it could be shown that partial oxidation of the applied phosphine ligand was beneficial for the course of the reaction, presumably by stabilizing the active catalyst. Reaction profiles and catalyst poisoning experiments were used to characterize the catalyst, the results of which indicate a homogeneous metal complex as the active species.

Purified mCPBA, a Useful Reagent for the Oxidation of Aldehydes

Purified mCPBA is a useful reagent for the oxidation of several classes of aldehyde. Although linear unbranched aliphatic aldehydes are oxidized to the corresponding carboxylic acids, α-branched ones undergo Baeyer–Villiger oxidation to formates. α-Branched α,β-unsaturated aldehydes provide enolformates and/or epoxides, which can be saponified to α-hydroxy ketones with shortening of the carbon chain by 1 carbon. Unbranched α,β-unsaturated aldehydes undergo an interesting Baeyer–Villiger oxidation/epoxidation/formate migration/BV oxidation cascade, which results in formyl-protected hydrates with an overall loss of two carbon atoms.

Organocatalytic Enantioselective Protonation for Photoreduction of Activated Ketones and Ketimines Induced by Visible Light

The first catalytic asymmetric photoreduction of 1,2-diketones and α-keto ketimines under visible light irradiation is reported. A transition-metal-free synergistic catalysis platform harnessing dicyanopyrazine-derived chromophore (DPZ) as the photoredox catalyst and a non-covalent chiral organocatalyst is effective for these transformations. With the flexible use of a chiral Br?nsted acid or base in H+ transfer interchange to control the elusive enantioselective protonation, a variety of chiral α-hydroxy ketones and α-amino ketones were obtained with high yields and enantioselectivities.

Internal Alkyne Regio- and Chemoselectivity using a Zwitterionic N-Heterocyclic Carbene Gold Catalyst in a Silver-Free Alkyne Hydration Reaction

An alkyne hydration of terminal and internal alkynes is reported using a zwitterionic N-heterocyclic carbene gold catalyst [(BNHC)Au(SMe2)] in the absence of silver and Br?nsted acid additives. The hydration demonstrates good regioselectivity in alkyne hydration and chemoselectivity for internal alkynes vs. terminal. In addition, (BNHC)Au(SMe2) performs a propargyl alcohol hydration to predominantly form α-hydroxymethyl ketone over the more common Meyer–Schuster rearrangement product. While complex (BNHC)Au(SMe2) is active without silver additives, addition of silver hexafluoroantimonate (AgSbF6) increases reaction rate and decreases selectivity for internal alkyne hydration over terminal substrates. To the best of our knowledge, the rate enhancement of (BNHC)Au(SMe2) by AgSbF6is the first such demonstration of a silver effect for a “halide-free” Au catalyst. (Figure presented.).