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Usage

Uses

Used in Pharmaceutical Industry:
(S)-4-phenyl-2-(2-((S)-p-tolylsulfinyl)phenyl)-4,5-dihydrooxazole is used as a key intermediate for the development of pharmaceuticals. Its unique structure and properties allow for the creation of various biologically active molecules, contributing to the advancement of new drug candidates.
Used in Agrochemical Industry:
In the agrochemical industry, (S)-4-phenyl-2-(2-((S)-p-tolylsulfinyl)phenyl)-4,5-dihydrooxazole is employed as a building block for the synthesis of agrochemicals. Its versatile chemical structure enables the development of novel compounds with potential applications in agriculture, such as pesticides and herbicides.
Used in Organic Synthesis:
(S)-4-phenyl-2-(2-((S)-p-tolylsulfinyl)phenyl)-4,5-dihydrooxazole is also used as a crucial component in organic synthesis. Its presence in the synthesis process allows for the creation of a diverse range of organic compounds with various applications across different industries.

Upstream product

• 50444-99-0 (1R,2S,5R)-menthyl-(S)-p-toluenesulfinate 
• 321848-64-0 (4S)-2-(2-bromophenyl)-4-phenyl-4,5-dihydro-1,3-oxazole 
• 91796-57-5 (1S,2R,5S,R_S)-(+)-Menthyl toluene-p-sulfinate 
• 20989-17-7 (2S)-2-phenylglycinol 
• 7154-66-7 2-bromobenzoic acid chloride 
• 88-65-3 2-bromobenzoic-acid 
• 1517-82-4 (1R,2S,5R,SS)-(-)-menthyl p-toluenesulfinate 

Relevant academic research and scientific papers

New chiral sulfoxide ligands in catalytic asymmetric Diels-Alder reactions: Double acceleration by the chiralities of the sulfoxides and oxazolines

New chiral sulfoxide ligands which are useful for catalytic asymmetric Diels-Alder reactions have been developed. The new ligands involve a chiral sulfinyl function and a 1,3-oxazoline ring with an asymmetric carbon center, in which the chiral sulfinyl group has been revealed to play a crucial role in achieving high enantioselectivity in asymmetric Diels-Alder reactions. Among the Lewis acid catalysts employed, magnesium iodide provided the highest chemical and stereochemical efficiency in the cycloaddition reactions. A mechanistic pathway for the asymmetric synthesis is proposed on the basis of the stereochemical outcomes obtained.

Sulfoxide ligand metal catalyzed oxidation of olefins

The enantioselective synthesis of isochroman motifs has been accomplished via Pd(II)-catalyzed allylic C—H oxidation from terminal olefin precursors. Critical to the success of this goal was the development and utilization of a novel chiral aryl sulfoxide-oxazoline (ArSOX) ligand. The allylic C—H oxidation reaction proceeds with the broadest scope and highest levels asymmetric induction reported to date (avg. 92% ee, 13 examples ≥90% ee). Additionally, C(sp3)-N fragment coupling reaction between abundant terminal olefins and N-triflyl protected aliphatic and aromatic amines via Pd(II)/sulfoxide (SOX) catalyzed intermolecular allylic C—H amination is disclosed. A range of 52 allylic amines are furnished in good yields (avg. 76%) and excellent regio- and stereoselectivity (avg. >20:1 linear:branched, >20:1 E:Z). For the first time, a variety of singly activated aromatic and aliphatic nitrogen nucleophiles, including ones with stereochemical elements, can be used in fragment coupling stiochiometries for intermolecular C—H amination reactions.

Enantioselective Allylic C?H Oxidation of Terminal Olefins to Isochromans by Palladium(II)/Chiral Sulfoxide Catalysis

The enantioselective synthesis of isochroman motifs has been accomplished by palladium(II)-catalyzed allylic C?H oxidation from terminal olefin precursors. Critical to the success of this goal was the development and utilization of a novel chiral aryl sul