57132-23-7

Upstream product

• 16927-82-5 (E)-4-(2-methylphenyl)but-3-en-2-one 
• 4549-82-0 (E)-2-methylcinnamaldehyde 
• 75-16-1 methylmagnesium bromide 
• 501922-06-1 (E)-3-(2-methylphenyl)-2-propenol 
• 24393-48-4 ethyl trans-2-methylcinnamate 
• 529-20-4 2-methylphenyl aldehyde 

Downstream Products

• 1587713-38-9 (Z)-4-(4-(o-tolyl)but-3-en-2-yl)morpholine 
• 1587713-20-9 (E)-4-(4-(o-tolyl)but-3-en-2-yl)morpholine 
• 767-59-9 1-Methylinden 
• 1380341-59-2 (E)-ethyl 2-methyl-4-o-tolylbut-3-enoate 
• 1054585-73-7 (2R,3E)-4-(2-methylphenyl)-3-buten-2-ol 

Relevant academic research and scientific papers

Chemoselective Luche-Type Reduction of α,β-Unsaturated Ketones by Magnesium Catalysis

The chemoselective reduction of α,β-unsaturated ketones by use of an economic and readily available Mg catalyst has been developed. Excellent yields for a wide range of ketones have been achieved under mild reaction conditions, short times, and low catalyst loadings (0.2-0.5 mol %).

Stereodivergent Pd/Cu Catalysis for the Dynamic Kinetic Asymmetric Transformation of Racemic Unsymmetrical 1,3-Disubstituted Allyl Acetates

A stereodivergent Pd/Cu catalyst system has been developed for the unprecedented dynamic kinetic asymmetric transformation (DyKAT) of racemic unsymmetrical 1,3-disubstituted allylic acetates with prochiral aldimine esters. A series of α,α-disubstituted α-amino acids bearing vicinal stereocenters were easily prepared with excellent enantioselectivities (up to >99% ee) and diastereoselectivities (up to >20:1 dr). Moreover, all four stereoisomers of the product can be readily obtained simply by switching the configurations of the two chiral metal catalysts. Furthermore, the present work highlights the power of synergistic Pd/Cu catalysis consisting of two common bidentate chiral ligands for stereodivergent synthesis.

Carbocation catalysed ring closing aldehyde-olefin metathesis

A highly efficient aldehyde-olefin metathesis catalysed by the carbocation, 4-phenylphenyl-diphenylmethylium ion, has been developed. This protocol is characterized by high yields, low catalyst loading (down to 2 mol%), good functional group compatibility and mild reaction conditions.

Facile synthesis of Z -alkenes via uphill catalysis

Catalytic access to thermodynamically less stable Z-alkenes has recently received considerable attention. These approaches have relied upon kinetic control of the reaction to arrive at the thermodynamically less stable geometrical isomer. Herein, we present an orthogonal approach which proceeds via photochemically catalyzed isomerization of the thermodynamic E-alkene to the less stable Z-isomer which occurs via a photochemical pumping mechanism. We consider two potential mechanisms. Importantly, the reaction conditions are mild, tolerant, and operationally simple and will be easily implemented.

Chemoselective conjugate reduction of α,β-unsaturated ketones catalyzed by rhodium amido complexes in aqueous media

Although a notable feature of Noyori's Ru-TsDPEN complex is that the transfer hydrogenation reaction is highly chemoselective for the C-O functional group and tolerant of alkenes, our early report indicated that the chemoselectivity could be switched from C-O to C-C bonds in the transfer hydrogenation of activated α,β-unsaturated ketones. Now we have found that a variety of α,β-unsaturated ketones, even without other electron-withdrawing functional groups, could be reduced on the alkenic double bonds with high selectivities employing amido-rhodium hydride complex in aqueous media, and up to 100% chemoselectivity has been achieved. It is notable that the chemoselectivity was improved significantly on going from organic solvent to water. Moreover, a 1,4-addition mechanism has been proposed on the basis of the corresponding experimental details and computational analysis.

Enantiomerically pure allylic alcohols: preparation by Candida parapsilosis ATCC 7330 mediated deracemisation

Biocatalytic deracemisation of racemic allylic alcohols by whole cells of Candida parapsilosis ATCC 7330 resulted in the formation of the (R)-enantiomers in high enantiomeric excesses (up to >99%) and isolated yields (up to 79%).