93397-58-1

Upstream product

• 75-75-2 methanesulfonic acid 
• 93-55-0 1-phenyl-propan-1-one 
• 591-51-5 phenyllithium 
• 5650-40-8 (S)-2-hydroxypropiophenone 
• 124-63-0 methanesulfonyl chloride 
• 100560-59-6 (S)-2-(1-ethoxyethoxy)-1-phenyl-1-propanone 

Downstream Products

• 37778-99-7 (S)-2-phenyl-1-propanol 

Relevant academic research and scientific papers

C?N Axial Chiral Hypervalent Iodine Reagents: Catalytic Stereoselective α-Oxytosylation of Ketones

A simple synthesis of a library of novel C?N axially chiral iodoarenes is achieved in a three-step synthesis from commercially available aniline derivatives. C?N axial chiral iodine reagents are rarely investigated in the hypervalent iodine arena. The potential of the novel chiral iodoarenes as organocatalysts for stereoselective oxidative transformations is assessed using the well explored, but challenging stereoselective α-oxytosylation of ketones. All investigated reagents catalyse the stereoselective oxidation of propiophenone to the corresponding chiral α-oxytosylated products with good stereochemical control. Using the optimised reaction conditions a wide range of products was obtained in generally good to excellent yields and with good enantioselectivities.

Catalytic enantioselective α-tosyloxylation of ketones using iodoaryloxazoline catalysts: Insights on the stereoinduction process

A family of iodooxazoline catalysts was developed to promote the iodine(III)-mediated α-tosyloxylation of ketone derivatives. The α-tosyloxy ketones produced are polyvalent chiral synthons. Through this study, we have unearthed a unique mode of stereoinduction from the chiral oxazoline moiety, where the stereogenic center alpha to the oxazoline oxygen atom is significant. Computational chemistry was used to rationalize the stereoinduction process. The catalysts presented promote currently among the best levels of activity and selectivity for this transformation. Evaluation of the scope of the reaction is presented.

Enantioselective α-tosyloxylation of ketones catalyzed by spirobiindane scaffold-based chiral iodoarenes

Enantiomerically pure iodoarene (S)-2 and its derivatives (S)-3 to (S)-18 with a spirobiindane scaffold have been synthesized. The evaluation of these new chiral iodoarenes as catalysts in the enantioselective α-tosyloxylation of ketones was performed using m-CPBA as a stoichiometric oxidant, and the synthetically useful α-tosyloxylated ketones were obtained in up to 58% enantiomeric excess (ee).

REDUCTIVE PINACOL-TYPE REARRANGEMENT OF GHIRAL α-MESYLOXY KETONES PROMOTED BY ORGANOALUMINIUM COMPOUNDS

Reductive pinacol type rearrangement of chiral α-mesyloxy ketones was effected by organoaluminiums (DIBAL in combination with Et3Al or Et2AlCl) leading to enantiomerically pure 2-aryl- or 2-alkenyl-1-propanols.