89818-52-0

Upstream product

• 87905-06-4 1-phenylethyl 2-pyridyl sulfoxide 
• 1823-91-2 (S)-α-phenylpropionitrile 
• 74-86-2 acetylene 
• 15260-65-8 2-(1-phenylvinyl)pyridine 
• 20780-53-4 (R)-Styrene oxide 
• 91-02-1 phenyl(pyridin-2-yl)methanone 
• 98-98-6 2-Picolinic acid 
• 148493-07-6 N-methoxy-N-methyl-2-pyridinecarboxamide 
• 89818-50-8 (+)-(R)-1-Phenyl ethyl 2-pyridyl sulfide 

Relevant academic research and scientific papers

Photoenzymatic Hydrogenation of Heteroaromatic Olefins Using ‘Ene’-Reductases with Photoredox Catalysts

Flavin-dependent ‘ene’-reductases (EREDs) are highly selective catalysts for the asymmetric reduction of activated alkenes. This function is, however, limited to enones, enoates, and nitroalkenes using the native hydride transfer mechanism. Here we demonstrate that EREDs can reduce vinyl pyridines when irradiated with visible light in the presence of a photoredox catalyst. Experimental evidence suggests the reaction proceeds via a radical mechanism where the vinyl pyridine is reduced to the corresponding neutral benzylic radical in solution. DFT calculations reveal this radical to be “dynamically stable”, suggesting it is sufficiently long-lived to diffuse into the enzyme active site for stereoselective hydrogen atom transfer. This reduction mechanism is distinct from the native one, highlighting the opportunity to expand the synthetic capabilities of existing enzyme platforms by exploiting new mechanistic models.

Versatile C(sp2)?C(sp3) Ligand Couplings of Sulfoxides for the Enantioselective Synthesis of Diarylalkanes

The reaction of chiral (hetero)aryl benzyl sulfoxides with Grignard reagents affords enantiomerically pure diarylalkanes in up to 98 % yield and greater than 99.5 % enantiomeric excess. This ligand coupling reaction is tolerant to multiple substitution patterns and provides access to diverse areas of chemical space in three operationally simple steps from commercially available reagents. This strategy provides orthogonal access to electron-deficient heteroaromatic compounds, which are traditionally synthesized by transition metal catalyzed cross-couplings, and circumvents common issues associated with proto-demetalation and β-hydride elimination.

DiPAMP's big brother "i-Pr-SMS-Phos" exhibits exceptional features enhancing rhodium(I)-catalyzed hydrogenation of olefins

Switching Knowles DiPAMP's {DiPAMP = l,2-bis[(o-anisyl)(phenyl)phosphino] ethane} MeO groups with i-PrO ones led to the iPr-SMS-Phos {i-Pr-SMS-Phos = l,2-bis[(o-isopropoxyphenyl)(phenyl)phosphino]ethane} ligand which displayed a boosted catalyst activity coupled with an enhanced enantioselectivity in the rhodium(I)catalyzed hydrogenation of a wide-range of representative olefinic substrates (dehydro-a-amido acids, itaconates, acrylates, enamides, enol acetates, α,α-diarylethylenes, etc). The rhodium(I)-(i-PrSMS-Phos) catalytic profile was investigated revealing its structural attributes and robustness, and in contrast to the usual trend, 31P NMR analysis revealed that its methyl (Z)-α-acetamidocinnamate (MAC) adduct consisted of a reversed diastereomeric ratio of 1.4:1 in favour of the most reactive diastereomer.

OPTICALLY ACTIVE HETEROAROMATIC COMPOUNDS: X. THE SYNTHESIS OF OPTICALLY ACTIVE DISUBSTITUTED PYRIDINES: AN OVERVIEW

An extended study on the synthesis of optically disubstituted pyridines containing a single chiral substituent with at least one chirality centre adjacent to the heterocyclic ring, carried out by the authors over the past few years is reported.A special c

Ligand Coupling within ?-Sulphurane Intermediates formed in the Reaction of Benzyl 2-Pyridyl and Related Sulphoxides with Grignard reagents

The reaction of benzyl or 1-phenylethyl 2-pyridyl sulphoxide (1) or (18) with a Grignard reagent was found to give the ligand-coupling product, i.e., 2-benzylpyridine or 2-(1-phenylethyl)pyridine (2) or (22) in excellent yield.This coupling reaction was found to proceed whithin the ?-sulphurane formed as an intermediate upon treatment of benzyl 2-pyridyl and related sulphoxides with a Grignard reagent.The stereochemical course of this coupling reaction involves complete retention at the benzylic carbon.

LIGAND COUPLING THROUGH ?-SULFURANE --- COMPLETE RETENTION OF CONFIGURATION OF 1-PHENYLETHYL GROUP IN THE REACTION OF 1-PHENYLETHYL 2-PYRIDYL SULFOXIDE WITH GRIGNARD REAGENT

The reaction of benzyl or 1-phenylethyl 2-pyridyl sulfoxide with Grignard reagent proceeds via a ?-sulfurane as an intermediate to give the coupling product, 2-benzylpyridine or 2-(1-phenylethyl)pyridine in quantitative yield.Stereochemistry for this reaction is complete retention at the benzylic carbon atom.