191347-98-5

Usage

Molecular Weight

144.17 g/mol

Stereochemistry

Chiral compound with (R)-enantiomer

Structure

A six-membered cyclic ether with a carbonyl group at the 5-position, two methyl groups at the 2-position, and an additional oxygen atom in the ring.

Pharmaceutical synthesis

Used as a versatile building block in the synthesis of various pharmaceuticals.

Agrochemical synthesis

Employed in the production of agrochemicals.

Fine chemicals production

Utilized as a reagent in the production of fine chemicals.

Organic synthesis

Serves as a reagent in various organic synthesis processes.

Industry Relevance

(R)-enantiomer has specific applications in the pharmaceutical and chemical industries due to its unique stereochemistry and reactivity.

Optical Activity

Exhibits optical activity, which is the ability to rotate the plane of polarized light.

Solubility

Generally soluble in organic solvents such as ethanol, methanol, and acetone.

Stability

Stable under normal conditions, but sensitive to heat, light, and moisture.

Hazards

May be harmful if inhaled, ingested, or absorbed through the skin. It is important to handle with care and use appropriate safety measures.

Upstream product

• 1003-83-4 2,2-dimethyl-4,7-dihydro-1,3-dioxepin 
• 201230-82-2 carbon monoxide 

Downstream Products

• 191348-02-4 (R)-3-Benzyloxymethyl-dihydro-furan-2-one 
• 191348-01-3 (R)-3-Benzyloxymethyl-2-methoxy-tetrahydro-furan 

Relevant academic research and scientific papers

Fine-tunable monodentate phosphoroamidite and aminophosphine ligands for Rh-catalyzed asymmetric hydroformylation

A biaryl-based monophosphoroamidite L1-L4a-f and aminophosphine L5-L7a-f ligand library was screened in the Rh-catalyzed asymmetric hydroformylation of several vinylarenes and heterocyclic olefins. Our results indicate that the selectivity is strongly dependent on the ligand parameters and on the substrate type. Enantioselectivities (up to 46%) were moderate in the hydroformylation of several vinylarenes S1-S5 and promising (up to 58%) for the more challenging heterocyclic olefins S6-S9.

Rh-catalyzed asymmetric hydroformylation of heterocyclic olefins using chiral diphosphite ligands. Scope and limitations

(Chemical Equation Presented) We used a series of diphosphite ligands to study the effect of the ligand backbone, the length of the bridge, and the substituents of the biphenyl moieties and determine the scope of this type of ligand in the Rh-catalyzed asymmetric hydroformylation of several hetereocylic olefins. By carefully selecting the ligand components, we achieved high chemo-, regio-, and enantioselectivities in different substrate types. Unprecedentedly high enantioselectivities for five-membered heterocyclic olefins were therefore obtained. Note that both enantiomers of the hydroformylation products can be synthesized using the same ligand by a simple substrate change. For the seven-membered heterocyclic dioxepines, our results are among the best obtained. Also, both enantiomers of the hydroformylation products can be obtained by using pseudoenantiomer ligands or by carefully tuning the ligand parameters.

Asymmetric Hydroformylation of Heterocyclic Olefins Catalyzed by Chiral Phosphine-Phosphite-Rh(I) Complexes

Asymmetric hydroformylation of heterocyclic olefins catalyzed by phosphine-phosphite-Rh(I) complexes has been investigated. Hydroformylation of symmetrical heterocyclic olefins such as 2,5-dihydrofuran, 3-pyrroline derivatives, and 4,7-dihydro-1,3-dioxepin derivatives afforded the optically active aldehydes as single products in 64-76% ee. Unsymmetrical substrates such as 2,3-dihydrofuran and N-(tert-butoxycarbonyl)-2-pyrroline gave a mixture of regioisomers. From N-(tert-butoxycarbonyl)-2-pyrroline was obtained N-(tert-butoxycarbonyl)pyrrolidine-2-carbaldehyde in 97% ee. The hydroformylation products from 2,5-dihydrofuran and N-(tert-butoxycarbonyl)-3-pyrroline have the opposite configurations to those from 2,3-dihydrofuran and N-(tert-butoxycarbonyl)-2-pyrroline, respectively, with the same catalyst. The new phosphine-phosphite ligand (R,S)-3,3′-Me2-BINAPHOS [= (A)-2-(diphenylphosphino)-1,1′-binaphthalen-2′-yl (S)-3,3′-dimethyl-1,1′-binaphthalene-2,2′-diyl phosphite] was prepared and its hydridorhodium complex was characterized by NMR spectroscopy. Using (R,S)-3,3′-Me2-BINAPHOS as a ligand, the enantioselectivity was improved for some substrates. In addition, higher catalytic activity was observed with this ligand for most of the substrates employed.