103108-05-0

Upstream product

• 103754-06-9 2-(1,2-dibromo-propyl)-anisole 
• 201230-82-2 carbon monoxide 
• 612-15-7 o-methoxystyrene 
• 68-12-2 N,N-dimethyl-formamide 
• 135-02-4 ortho-anisaldehyde 
• 42432-44-0 2-(2-methoxyphenyl)-2-methyloxirane 
• 579-74-8 2-Methoxyacetophenone 
• 4009-98-7 (methoxymethyl)triphenylphosphonium chloride 
• 191725-62-9 C₁₁H₁₄O₂ 
• 183583-04-2 2-(2-chlorophenyl)propanal 
• 6380-21-8 2-(prop-1-enyl)phenol 
• 10577-44-3 2-(1-propenyl)anisole 

Downstream Products

• 103108-23-2 anti-ethyl 3-hydroxy-4-(2-methoxyphenyl)dithiopentanoate 
• 103108-23-2 syn-ethyl 3-hydroxy-4-(2-methoxyphenyl)dithiopentanoate 
• 4720-31-4 N-<2-Methoxy-β-methyl-phenaethyl>-3-amino-propanol-(1) 
• 1224962-08-6 (R)-2-(2-methoxyphenyl)-2-methyl-4,4-bis(phenylsulfonyl)butanal 
• 1393802-67-9 (R)-2-(2-methoxyphenyl)-1-oxopropan-2-yl benzoate 
• 1431642-30-6 C₁₈H₂₄N₂O₄ 
• 1417328-64-3 dimethyl (2-(2-methoxyphenyl)propanoyl)phosphonate 
• 1417328-82-5 dimethyl ((1R,2R)-1-hydroxy-2-(2-methoxyphenyl)propyl)phosphonate 
• 1417329-01-1 dimethyl (1-hydroxy-2-(2-methoxyphenyl)propyl)phosphonate 
• 1417329-01-1 dimethyl (1-hydroxy-2-(2-methoxyphenyl)propyl)phosphonate 

Relevant academic research and scientific papers

Mechanism of the Bis(imino)pyridine-Iron-Catalyzed Hydromagnesiation of Styrene Derivatives

Iron-catalyzed hydromagnesiation of styrene derivatives offers a rapid and efficient method to generate benzylic Grignard reagents, which can be applied in a range of transformations to provide products of formal hydrofunctionalization. While iron-catalyzed methodologies exist for the hydromagnesiation of terminal alkenes, internal alkynes, and styrene derivatives, the underlying mechanisms of catalysis remain largely undefined. To address this issue and determine the divergent reactivity from established cross-coupling and hydrofunctionalization reactions, a detailed study of the bis(imino)pyridine iron-catalyzed hydromagnesiation of styrene derivatives is reported. Using a combination of kinetic analysis, deuterium labeling, and reactivity studies as well as in situ 57Fe M?ssbauer spectroscopy, key mechanistic features and species were established. A formally iron(0) ate complex [iPrBIPFe(Et)(CH2a?CH2)]- was identified as the principle resting state of the catalyst. Dissociation of ethene forms the catalytically active species which can reversibly coordinate the styrene derivative and mediate a direct and reversible β-hydride transfer, negating the necessity of a discrete iron hydride intermediate. Finally, displacement of the tridentate bis(imino)pyridine ligand over the course of the reaction results in the formation of a tris-styrene-coordinated iron(0) complex, which is also a competent catalyst for hydromagnesiation.

Mild Iridium-Catalysed Isomerization of Epoxides. Computational Insights and Application to the Synthesis of β-Alkyl Amines

The isomerization of epoxides to aldehydes using the readily available Crabtree's reagent is described. The aldehydes were transformed into synthetically useful amines by a one-pot reductive amination using pyrrolidine as imine-formation catalyst. The reactions worked with low catalyst loadings in very mild conditions. The procedure is operationally simple and tolerates a wide range of functional groups. A DFT study of its mechanism is presented showing that the isomerization takes place via an iridium hydride mechanism with a low energy barrier, in agreement with the mild reaction conditions. (Figure presented.).

Direct Synthesis of α-Allenols from TMS-Protected Alkynes and Aldehydes Mediated by Tetrabutylammonium Fluoride

A unique chemoselective synthesis of α-allenic alcohols is presented. Tetrabutylammonium fluoride (TBAF) mediated this transformation under mild reaction conditions. A range of functional groups is well-tolerated in this reaction, while affording adducts

Dynamic kinetic asymmetric amination of alcohols: From a mixture of four isomers to diastereo- and enantiopure α-branched amines

The first dynamic kinetic asymmetric amination of alcohols via borrowing hydrogen methodology is presented. Under the cooperative catalysis by an iridium complex and a chiral phosphoric acid, α-branched alcohols that exist as a mixture of four isomers undergo racemization by two orthogonal mechanisms and are converted to diastereo- and enantiopure amines bearing adjacent stereocenters. The preparation of diastereo- and enantiopure 1,2-amino alcohols is also realized using this catalytic system.

Dynamic kinetic resolution of 2-phenylpropanal derivatives to yield β-chiral primary amines via bioamination

The amination of racemic α-chiral aldehydes, 2-phenylpropanal derivatives, was investigated employing ω-transaminases. By medium and substrate engineering the optical purity of the resulting β-chiral chiral amine could be enhanced to reach optical purities up to 99% ee. Using enantiocomplementary ω-transaminases allowed us to access the (R)- as well as the (S)-enantiomer in most cases. It is important to note that the stereopreference of the ω-transaminases found for α-chiral aldehydes did not correlate with the stereopreference previously observed for the amination of methyl ketones. In one case the stereopreference switched even upon exchanging a methyl substituent to a methoxy group.

Beyond classical reactivity patterns: Hydroformylation of vinyl and allyl arenes to valuable β- And γ-aldehyde intermediates using supramolecular catalysis

In this study, we report on properties of a series of rhodium complexes of bisphosphine and bisphosphite L1-L7 ligands, which are equipped with an integral anion binding site (the DIM pocket), and their application in the regioselective hydroformylation of vinyl and allyl arenes bearing an anionic group. In principle, the binding site of the ligand is used to preorganize a substrate molecule through noncovalent interactions with its anionic group to promote otherwise unfavorable reaction pathways. We demonstrate that this strategy allows for unprecedented reversal of selectivity to form otherwise disfavored β-aldehyde products in the hydroformylation of vinyl 2- and 3-carboxyarenes, with chemo- and regioselectivity up to 100%. The catalyst has a wide substrate scope, including the most challenging substrates with internal double bonds. Coordination studies of the catalysts under catalytically relevant conditions reveal the formation of the hydridobiscarbonyl rhodium complexes [Rh(Ln)(CO)2H]. The titration studies confirm that the rhodium complexes can bind anionic species in the DIM binding site of the ligand. Furthermore, kinetic studies and in situ spectroscopic investigations for the most active catalyst give insight into the operational mode of the system, and reveal that the catalytically active species are involved in complex equilibria with unusual dormant (reversibly inactivated) species. In principle, this involves the competitive inhibition of the recognition center by product binding, as well as the inhibition of the metal center via reversible coordination of either a substrate or a product molecule. Despite the inhibition effects, the substrate preorganization gives rise to very high activities and efficiencies (TON > 18‰000 and TOF > 6000 mol mol-1 h-1), which are adequate for commercial applications.

Supramolecular control of selectivity in hydroformylation of vinyl arenes: Easy access to valuable β-aldehyde intermediates

Go against the flow! A rationally designed regioselective hydroformylation catalyst, [Rh/L], in which noncovalent ligand-substrate interactions allow the unprecedented reversal of selectivity from the typical α-aldehyde to the otherwise unfavored product β-aldehyde, is reported. This catalytic system opens up novel and sustainable synthetic pathways to important intermediates for the fine-chemicals industry.

Piperidine and tetrahydropyridine derivatives

A class of substituted piperidine and tetrahydropyridine derivatives, linked through the 4-position thereof via an alkylene chain to a fused bicyclic heteroaromatic moiety such as indolyl, and further substituted at the 1-position by an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl-alkyl, aryl-alkyl or heteroaryl-alkyl moiety, are selective agonists of 5-HT1 -like receptors, being potent agonists of the human 5-HT1Dα; receptor subtype whilst processing at least a 10-fold selective affinity for the 5-HT1Dα; receptor subtype relative to the 5-HT1Dβ; subtype; they are therefore useful in the treatment and/or prevention of clinical conditions, in particular migraine and associated disorders, for which a subtype-selective agonist of 5-HT1D receptors is indicated, whilst eliciting fewer side-effects, notably adverse cardiovascular events, than those associated with non-subtype-selective 5-HT1D receptor agonists.