88196-06-9

Upstream product

• 873-66-5 1-propenylbenzene 
• 1846-29-3 1,3-diphenyl-2-methylpropane-1,3-dione 
• 100560-59-6 (S)-2-(1-ethoxyethoxy)-1-phenyl-1-propanone 
• 123485-26-7 (1S,2R)-1,2-diacetoxy-1-phenylpropane 
• 766-90-5 cis-1-phenyl-1-propylene 
• 113-24-6 sodium pyruvate 
• 100-52-7 benzaldehyde 
• 579-07-7 1-Phenylpropane-1,2-dione 
• 4541-87-1 cis-1-phenylpropene oxide 
• 5650-40-8 (S)-2-hydroxypropiophenone 
• 75927-49-0 pinacol vinylboronate 
• 4518-66-5 (1S,2S)-(-)-1-phenyl-1-propene oxide 
• 90-63-1 (RS)-1-hydroxy-1-phenylpropan-2-one 
• 53439-91-1 (S)-phenylacetylcarbinol 

Downstream Products

• 145950-20-5 Acetic acid (1S,2R)-2-chloro-1-methyl-2-phenyl-ethyl ester 
• 799246-07-4 (4S,5S)-4-methyl-5-phenyl-1,3,2-dioxathiolane-2-oxide 
• 37577-28-9 (1S,2R)-(+)-norphedrine 
• 37577-07-4 Norpseudoephedrine 
• 5265-18-9 (+/-)-cathinone 
• 55383-21-6 (1RS,2RS)-1-cyclohexyl-propane-1,2-diol 
• 21145-69-7 (1SR,2SR)-1-phenylpropane-1,2-diyl diacetate 
• 5650-40-8 (R)-2-hydroxy-1-phenylpropan-1-one 
• 40421-51-0 (1R,2R)-1-phenylpropane-1,2-diol 
• 90-63-1 (RS)-1-hydroxy-1-phenylpropan-2-one 
• 5650-40-8 (S)-2-hydroxypropiophenone 
• 100-52-7 benzaldehyde 
• 75-07-0 acetaldehyde 
• 103-79-7 1-phenyl-acetone 

Relevant academic research and scientific papers

A Protocol for NMR Analysis of the Enantiomeric Excess of Chiral Diols Using an Achiral Diboronic Acid Template

A practically simple derivatization protocol for determining the enantiopurity of chiral diols by 1H NMR spectroscopic analysis is described. Diols were treated with 0.5 equiv of 1,3-phenyldiboronic acid to afford mixtures of diastereomeric boronate esters whose homochiral/heterochiral ratios are an accurate reflection of the diol's enantiopurity.

Enantioselective, Stereoconvergent Resolution Copolymerization of Racemic cis-Internal Epoxides and Anhydrides

Unprecedented enantioselective resolution copolymerization of racemic cis-internal epoxides and anhydrides was mediated by dinuclear aluminum complexes with multiple chirality, affording optically active polyesters with two contiguous stereogenic centers, and the unreacted substrates in good enantioselectivity. Unexpected stereoconvergence is observed in this resolution copolymerization, where the selectivity factor for the enantioselective formation of copolymer significantly exceeds the kinetic resolution coefficient based on the unreacted epoxide at various conversions. Catalytic activity and copolymer enantioselectivity are strongly influenced by the phenolate ortho-substituents of the ligand set, as well as the axial linker and its chirality. An enantiopure binaphthol-linked bimetallic AlIII complex allows stereoconvergent access to the stereoregular semi-crystalline polyesters and a concomitant kinetic resolution of the epoxide substrates.

Electrochemically Tuned Oxidative [4+2] Annulation and Dioxygenation of Olefins with Hydroxamic Acids

This work represents the first [4+2] annulation of hydroxamic acids with olefins for the synthesis of benzo[c][1,2]oxazines scaffold via anode-selective electrochemical oxidation. This protocol features mild conditions, is oxidant free, shows high regioselectivity and stereoselectivity, broad substrate scope of both alkenes and hydroxamic acids, and is compatible with terpenes, peptides, and steroids. Significantly, the dioxygenation of olefins employing hydroxamic acid is also successfully achieved by switching the anode material under the same reaction conditions. The study not only reveals a new reactivity of hydroxamic acids and its first application in electrosynthesis but also provides a successful example of anode material-tuned product selectivity.

Iodine-Initiated Dioxygenation of Aryl Alkenes Using tert-Butylhydroperoxides and Water: A Route to Vicinal Diols and Bisperoxides

An environment-friendly and efficient dioxygenation of aryl alkenes for the construction of vicinal diols has been developed in water with iodine as the catalyst and tert-butylhydroperoxides (TBHPs) as the oxidant. The protocol was efficient, sustainable, and operationally simple. Detailed mechanistic studies indicated that one of the hydroxyl groups is derived from water and the other one is derived from TBHP. Additionally, the bisperoxides could be obtained in good yields with iodine as the catalyst, Na2CO3 as the additive, and propylene carbonate as the solvent, instead.

A One-Pot Two-Step Enzymatic Pathway for the Synthesis of Enantiomerically Enriched Vicinal Diols

Enantiomerically enriched 1,2-diols are prominent compounds that find numerous applications in organic chemistry. They are privileged building blocks for the synthesis of APIs (Active Pharmaceutical Ingredients), broadly used as chiral ligands in asymmetric catalysis, and efficient auxiliaries employed to control the stereochemical outcome of total synthesis. Among the number of strategies developed for the preparation of these molecules, enzyme mediated reactions have gained a crucial role in the toolbox of organic chemists for their high efficiency and sustainability. Herein we describe a one-pot two-step protocol designed by combining a thiamine diphosphate (ThDP)-dependent lyase and a NADH-dependent reductase. The ThDP-dependent acetoin:dichlorophenolindophenol oxidoreductase (Ao : DCPIP OR) is exploited to produce enantioenriched α-hydroxyketones through the benzoin-type condensation of methylacetoin with either aldehydes or activated ketones. The enantioenriched α-hydroxyketones undergo the selective reduction into the corresponding 1,2-diols in the same reaction mixture due to the addition of NAD+ and of the NADH-dependent acetylacetoin reductase (AAR). Sodium formate was selected as the sacrificial reductive reactant to generate and recycle in situ the precious NADH by formate-dehydrogenase. Unprecedented reported details on the cloning and expression of the AAR are reported as well.

A stand-alone cobalt bis(dicarbollide) photoredox catalyst epoxidates alkenes in water at extremely low catalyst load

The cobalt bis(dicarbollide) complex, Na[3,3′-Co(η5-1,2-C2B9H11) (Na[1]), is an effective photoredox catalyst for the oxidation of alkenes to epoxides in water. Advantageous features of Na[1] include its lack of photoluminescence, high solubility and surfactant behavior in aqueous media, as well as the donor ability of the carborane ligand and high oxidizing power of the Co4+/3+ couple. These features differentiate it from the well-known and widely used photosensitizer tris (2,2′-bipyridine) ruthenium(ii) ([Ru(bpy)3]2+), which also participates in electron transfer through an outer sphere mechanism. A comparison of the catalytic performance of [Ru(bpy)3]2+ with Na[1] for alkene photo-oxidation is fully in favor of Na[1], as the former shows very low or null efficiency. With a catalyst loading of 0.1 mol% conversions between 65-97% have been obtained in short reaction times, 15 minutes, with moderate selectivity for the corresponding epoxide, due to the formation of side products as diols. But when the catalyst loading is reduced to 0.01 mol%, the selectivity for the corresponding epoxide increased considerably, being the only compound formed after 15 minutes of reaction (selectivity >99%). High TON values have been obtained (TON = 8500) for the epoxidation of aromatic and aliphatic alkenes in water. We have verified that Na[3,3′-Co(η5-1,2-C2B9H11)2] acts as a photocatalyst in both the epoxidation of alkenes and in their hydroxylation in aqueous medium with a higher rate for epoxidation than for hydroxylation. Preliminary photooxidation tests using methyl oleate as the substrate led to the selective epoxidation of the double bond. These results represent a promising starting point for the development of practical methods for the processing of unsaturated fatty acids, such as the valorisation of animal fat waste using this sustainable photoredox catalyst. This journal is

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.

Atroposelective Synthesis of PINAP via Dynamic Kinetic Asymmetric Transformation

The atroposelective synthesis of PINAP ligands has been accomplished via a palladium-catalyzed C?P coupling process through dynamic kinetic asymmetric transformation. These catalytic conditions allow access to a wide variety of alkoxy- and benzyloxy-substituted PINAP ligands in high enantiomeric excess. The methods described in this communication afford valuable P,N ligands in good yields and high enantioselectivity using low catalyst loading. (Figure presented.).

Copper-Catalyzed Tandem Hydrocupration and Diastereo- and Enantioselective Borylalkyl Addition to Aldehydes

We report the copper-catalyzed stereoselective addition of in situ generated chiral boron-α-alkyl intermediates to various aldehydes including α,β-unsaturated aldehydes under mild conditions. This tandem and multicomponent method facilitated the synthesis of enantiomerically enriched 1,2-hydroxyboronates bearing contiguous stereocenters in good yield with high diastereo- and enantioselectivity up to a ratio greater than 98:2. In particular, α,β-unsaturated aldehydes were successfully used as electrophiles in Cu?H catalysis through 1,2-addition without significant reduction. The resulting 1,2-hydroxyboronates were used in various transformations.

Direct, high-yielding, one-step synthesis of vic-diols from aryl alkynes

An unprecedented, high yielding, direct, one-step synthesis of vic-diols from alkynes has been developed via metal-free, open-to-air dihydroboration with ammonia borane. The electronics of the alkyne and the reaction stoichiometry are critical for obtaining optimal yields of the 1,2-diol.