159652-77-4

Usage

Uses

Used in Pharmaceutical Synthesis:
(S)-2-phenyloxetane is used as an intermediate for the synthesis of pharmaceuticals and fine chemicals. Its unique structure and chiral properties allow for the creation of complex molecules with specific biological activities, making it a crucial component in the development of new drugs.
Used in Catalytic Epoxidation:
(S)-2-phenyloxetane has been studied for its potential application in catalytic epoxidation reactions. As a result, it may contribute to the development of more efficient and environmentally friendly chemical processes for producing epoxides, which are important intermediates in the chemical industry.
Used in Coordination Chemistry:
(S)-2-phenyloxetane has been investigated for its potential as a ligand in coordination chemistry. Its chiral nature and structural features make it a promising candidate for the development of novel catalysts and materials with enhanced performance and selectivity.
Used in Material Science:
(S)-2-phenyloxetane is also being explored for its role in the development of new materials and catalysts. Its unique properties may lead to the creation of advanced materials with specific applications in various industries, such as electronics, energy, and environmental protection.

Upstream product

• 18776-12-0 3-chloro-1-phenyl-propan-1-ol 
• 20780-53-4 (R)-Styrene oxide 
• 70775-39-2 dimethylsulfoxonium methylide 
• 936-59-4 3-chloropropiophenone 

Downstream Products

• 16133-83-8 (S)-2-phenyltetrahydrofuran 

Relevant academic research and scientific papers

Stereospecific consecutive epoxide ring expansion with dimethylsulfoxonium methylide

Figure presented. Consecutive ring-expansion reactions of oxiranes with dimethylsulfxonium methylide were studied experimentally and modeled computationally at the density functional theory (DFT) and second-order Moller-Plesset (MP2) levels of theory utilizing a polarizable continuum model (PCM) to account for solvent effects. While the epoxide to oxetane ring expansion requires 13-17 kcal mol-1 activation and occurs at elevated temperatures, the barriers for the ring expansions to oxolanes are higher (ca. 25 kcal mol-1) and require heating to 125 °C. Further expansions of these oxolanes to the six-membered oxanes are hampered by high barriers (ca. 40 kcal mol-1). We observe the complete conservation of the enantiomeric purities for the nucleophilic ring expansions of enantiomeric 2-mono- and 2,2-disubstituted epoxides and oxetanes with dimethylsulfoxonium methylide. This is a convenient general approach for the high-yielding preparation of optically active four- and five-membered cyclic ethers from oxiranes.

Asymmetric Synthesis of 2-Aryl Substituted Oxetanes by Enantioselective Reduction of β-Halogenoketones using Lithium Borohydride modified with N,N'-Dibenzoylcystine

Optically active 2-aryl substituted oxetanes are synthesised in high enantiomeric excesses (up to 89percent e.e.) via enantioselective reduction of β-halogenoketones with lithium borohydride using (R,R')-N,N'-dibenzoylcystine and t-butyl alcohols as ligands.