1008787-89-0

Upstream product

• 22966-19-4 trans-4'-methoxychalcone 
• 109-77-3 malononitrile 
• 100-52-7 benzaldehyde 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 5443-49-2 α-bromocinnamaldehyde 
• 77609-11-1 2-(3-(4-methoxyphenyl)-3-oxo-1-phenylpropyl)malononitrile 
• 959-23-9 4'-methoxychalcone 
• 2700-22-3 Benzylidenemalononitrile 
• 13422-77-0 3-(4-methoxy-phenyl)-3-oxo-propionic acid 

Relevant academic research and scientific papers

Highly Enantioselective Kinetic Resolution of Michael Adducts through N-Heterocyclic Carbene Catalysis: An Efficient Asymmetric Route to Cyclohexenes

A highly efficient strategy for the kinetic resolution of Michael adducts was realized using a chiral N-heterocyclic carbene catalyst. The kinetic resolution provides a new convenient route to single diastereomers of cyclohexenes and Michael adducts in good yields with high enantiomeric excesses (up to 99 % ee with a selectivity factor of up to 458). This “two flies with one swat” concept allows the synthesis of these two synthetically valuable compound classes at the same time by a single transformation.

Chloramphenicol base chemistry. Part 11: chloramphenicol base-derived thiourea-catalyzed enantioselective Michael addition of malononitrile to α,β-unsaturated ketones

The first chloramphenicol base-derived thiourea-catalyzed enantioselective Michael addition of malononitrile to α,β-unsaturated ketones is reported. The Michael adducts were obtained in good to excellent yields (up to 98% yield) and enantioselectivities (up to 94% ee). This reaction has a broad substrate scope to various α,β-unsaturated ketones. With this in mind, this methodology was successfully applied to the synthesis of a chiral piperidone, an advanced building block for dihydropyridinone P2X7 receptor antagonists.

Thieme Chemistry Journals Awardees - Where Are They Now? A Stereoselective Tripeptide Catalyst for Conjugate Addition Reactions of Acetophenones to Dicyanoolefins

Peptides of the type H-Pro-Pro-Xaa-NH 2 were evaluated as catalysts for conjugate addition reactions of acetophenones to cyanoolefins. Tripeptide H- d -Pro-Pro-Glu-NH 2 with a carboxylic acid moiety in the side chain of Xaa was ident

Organocatalytic Enantioselective Decarboxylative Michael Addition of β-Keto Acids to Dicyanoolefins and Disulfonylolefins

A convenient organocatalytic enantioselective decarboxylative Michael addition of β-keto acids to dicyanoolefins and disulfonylolefins is realized. In the presence of saccharide-derived chiral amino thioureas, the reaction proceeded smoothly to afford a wide range of the Michael adducts in 62–99% yield with 70–94% ee. Moreover, one of the chiral adducts obtained could be readily converted into the monofluorinated product in a total 68% yield over four steps with 85% ee. (Figure presented.).

Proline catalyzed enantioselective Michael additions of unmodified ketones to arylidines

A range of proline-catalyzed Michael additions of unmodified ketones to arylidenes have been examined to yield optically active γ-cyanoketones in excellent to moderate yields with low enantioselectivities.

Squaramide-catalyzed enantioselective Michael addition of malononitrile to chalcones

A highly enantioselective Michael addition of malononitrile to chalcones catalyzed by a chiral quinine-derived squaramide catalyst has been developed. This organocatalytic reaction at a very low catalyst loading (0.5 mol%) led to chiral γ-cyano carbonyl c

Enantioselective conjugate addition of malononitrile to chalcones promoted by α,α-L-diaryl prolinols: Noncovalent versus covalent catalysis?

The enantioselective conjugate addition of malononitrile to trans-chalcones has been investigated as a case study using easily available α,α-L-diaryl prolinols as promoters. Both experimental and computational results are consistent with a bifunctional no

Back to natural cinchona alkaloids: Highly enantioselective Michael addition of malononitrile to enones

An efficient and convenient highly enantioselective Michael addition of malononitrile to enones has been developed by using quinine as the organocatalyst. The adducts were isolated in excellent yield and high asymmetric induction (up to 95% ee). An easy r

Organocatalytic asymmetric direct Michael addition of aromatic ketones to alkylidenemalononitriles

The asymmetric direct Michael addition of aromatic ketones to highly active alkylidenemalononitriles was investigated by employing a chiral primary amine 9-amino-9-deoxyepicinchonine. In general modest to good enantioselectivities (71-84% ee) could be obtained in acceptable isolated yields (48-85%) for an array of substrates.