791809-35-3

Upstream product

• 104-53-0 3-phenyl-propionaldehyde 
• 96-22-0 pentan-3-one 
• 58547-32-3 anti-5-hydroxy-4-methyl-7-phenyl-3-heptanone 

Downstream Products

• 1356563-92-2 (1R,2S,4R,5S,6S)-2-ethyl-1-methyl-6-(2-phenylethyl)-4-phenyl-3-oxabicyclo[3.1.0]hexane 
• 1356563-88-6 1-((R)-{(1R,2S,3R)-2-[(S)-1-(benzyloxy)propyl]-1-chloro-2-methyl-3-(2-phenylethyl)cyclopropyl}sulfinyl)-4-methylbenzene 
• 1356563-84-2 (S)-1-[(1S,2R,3R)-2-chloro-1-methyl-3-(2-phenylethyl)-2-((R)-p-tolylsulfinyl)cyclopropyl]propan-1-ol 
• 1067615-05-7 C₁₅H₂₀O 
• 1312031-72-3 C₂₂H₂₇ClO₂S 
• 1312031-66-5 [(1S,2R,3R)-2-chloro-1-methyl-3-(2-phenylethyl)-2-((R)-p-tolylsulfinyl)cyclopropyl]-propan-1-one 

Relevant academic research and scientific papers

Site- and Enantioselective Iridium-Catalyzed Desymmetric Mono-Hydrogenation of 1,4-Dienes

The control of site selectivity in asymmetric mono-hydrogenation of dienes or polyenes remains largely underdeveloped. Herein, we present a highly efficient desymmetrization of 1,4-dienes via iridium-catalyzed site- and enantioselective hydrogenation. This methodology demonstrates the first iridium-catalyzed hydrogenative desymmetriation of meso dienes and provides a concise approach to the installation of two vicinal stereogenic centers adjacent to an alkene. High isolated yields (up to 96 %) and excellent diastereo- and enantioselectivities (up to 99:1 d.r. and 99 % ee) were obtained for a series of divinyl carbinol and divinyl carbinamide substrates. DFT calculations reveal that an interaction between the hydroxy oxygen and the reacting hydride is responsible for the stereoselectivity of the desymmetrization of the divinyl carbinol. Based on the calculated energy profiles, a model that simulates product distribution over time was applied to show an intuitive kinetics of this process. The usefulness of the methodology was demonstrated by the synthesis of the key intermediates of natural products zaragozic acid A and (+)-invictolide.

Preparation and regioselective SN2′ reaction of novel gem-difluorinated vinyloxiranes with RLi

A series of hitherto unknown 3,4-epoxy-1,1-difluorobutenes were prepared from the readily accessible α,β-epoxy ketones and these compounds were found to undergo regioselective SN2′ reactions with hard RLi nucleophiles occurring at the highly positively charged terminal fluorine-possessing sp2 carbon atom in quite sharp contrast to the cases of the corresponding nonfluorinated vinyloxiranes which only attained a low level of regioselectivity. Addition of HMPA substantially improved the products' olefinic stereoselectivity. Theoretical calculations were used to qualitatively explore the nature of selectivity in these reactions.