195832-90-7

Upstream product

• 100-42-5 styrene 
• 201230-82-2 carbon monoxide 
• 100-53-8 phenylmethanethiol 
• 129505-03-9 (2R)-N-(phenylacetyl)bornane-10,2-sultam 
• 195832-80-5 (R)-1-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-2-phenyl-propan-1-one 

Downstream Products

• 951-85-9 (S)-methyldesoxybenzoin 
• 58751-83-0 1,2-diphenylpropan-1-one 

Relevant academic research and scientific papers

Palladium-Catalyzed Enantioselective Thiocarbonylation of Styrenes

A highly enantioselective thiocarbonylation of styrenes with CO and thiols has been achieved by Pd catalysis, providing highly enantioenriched thioesters in good to excellent yields. Key to the successful execution of this reaction is the use of a chiral sulfoxide-(P-dialkyl)-phosphine (SOP) ligands. This thiocarbonylation proceeds smoothly under mild reaction conditions (1 atm CO and 0 °C) and displays broad substrate scope. Also demonstrated is that this transformation can be conducted using surrogates of CO, greatly increasing the safety aspects of running the reaction. The generality and utility of the method is manifested by its application to the synthetic transformations of thioester products and the direct acylation of cysteine-containing dipeptides. A primary mechanism was investigated and a plausible catalytic cycle was proposed.

Method for synthesizing thioester compounds through olefin insert carbonyl sulfide esterification (by machine translation)

The invention belongs to the field, and belongs to the field of chemical synthesis. The invention specifically relates to a method for synthesizing chiral or non-chiral thioester compounds through palladium-catalyzed olefin carbonyl sulfide esterification

Non-destructive Removal of the Bornanesultam Auxiliary in α-Substituted N-Acylbornane-10,2-sultams under Mild Conditions: An Efficient Synthesis of Enantiomerically Pure Ketones and Aldehydes

α-Substituted N-acylbornane-10,2-sultams 6, 9, and 10 can be converted into enantiomerically pure ketones 5, 13, and 14, respectively, via a two-step procedure involving a known mercaptolysis reaction followed by an -mediated coupling of the resulting S-benzyl thioesters with Grignard reagents.Furthermore, enantiomerically pure aldehydes 23 can be obtained from α-substituted N-acylbornane-10,2-sultams 6 via a one-step reduction with (i-Bu)2AlH.No epimerization at the α-chiral center is observed during the cleavage reaction whereby the chiral auxiliary, bornane-10,2-sultam 1 or ent-1, was recovered.By using this methodology, several natural products or precursors thereof can be prepared.