495395-77-2

Upstream product

• 28557-00-8 phenylzinc chloride 
• 100-39-0 benzyl bromide 
• 591-51-5 phenyllithium 
• 103-80-0 phenylacetyl chloride 
• 646516-78-1 5-Oxo-bicyclo[4.2.0]octane-1-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 
• 51012-66-9 2-benzyl-2-bromoacetophenone 
• 100-58-3 phenylmagnesium bromide 
• 7474-65-9 (E)-2-phenylchalcone 

Relevant academic research and scientific papers

Rhodium-Catalyzed Enantioselective Isomerization of Secondary Allylic Alcohols

The first catalytic enantioselective isomerization of secondary allylic alcohols to access ketones with a α-tertiary stereocenter is presented. The racemic allylic alcohol substrates can be converted to the enantioenriched ketone products in a stereoconvergent fashion. The use of commercially available catalysts and mild reaction conditions makes this an attractive method in stereoselective synthesis.

Catalytic asymmetric cross-couplings of racemic α-bromoketones with arylzinc reagents

(Chemical Equation Presented) Nickel box: The first catalytic asymmetric method for cross-coupling arylzinc reagents with α-bromoketones has been developed (see scheme). This stereoconvergent carbon-carbon bond-forming process occurs under unusually mild conditions and without activators, thereby allowing the generation of potentially labile tertiary stereocenters.

Highly enantioselective synthesis of optically active ketones by iridium-catalyzed asymmetric hydrogenation

(Chemical Equation Presented) Close to perfect enantioselectivity (up to 99% ee, see scheme) is found for the formation of α-substituted ketones by the asymmetric hydrogenation of enones with an iridium-phosphinooxazoline catalyst. In an operationally simple process, both linear and cyclic substrates react well and afford the desired products in high yields. A wide variety of substituents are tolerated, thus making the method synthetically appealing.

Application of A Recyclable Pseudoephedrine Resin in Asymmetric Alkylations on Solid Phase

A pseudoephedrine resin has been successfully employed in asymmetric alkylations on solid phase. Immobilized pseudoephedrine amides are conveniently prepared by the one-step attachment of pseudoephedrine to Merrifield resin through the hydroxyl group and subsequent acylation on nitrogen. Deprotonation and alkylation of the resin-bound amides proceeds smoothly. Ketones and alcohols are cleaved from the resin in high enantiomeric excess and moderate to good overall yield. The parallel, asymmetric solid-phase synthesis of a small library of chiral ketones and alcohols has been carried out to illustrate the utility of the approach. Finally, the pseudoephedrine resin can be conveniently recycled and utilized with no significant loss in the yield or enantiomeric excess of the products.

Evaluation of a Pseudoephedrine Linker for Asymmetric Alkylations on Solid Phase

(Equation Presented) Immobilized pseudoephedrine amides have been conveniently prepared by attachment of pseudoephedrine to Merrifield resin and acylation on nitrogen. Deprotonation and alkylation of the resin bound amides proceeds smoothly. Products were cleaved from the resin to give ketones and alcohols in high enantiomeric excess and moderate to good overall yield.