1040232-82-3

Upstream product

• 2700-22-3 Benzylidenemalononitrile 
• 99-91-2 para-chloroacetophenone 
• 22966-22-9 (E)-1-(4-chlorophenyl)-3-phenyl-2-propen-1-one 
• 109-77-3 malononitrile 
• 17589-68-3 3-(4-chlorophenyl)-3-oxopropanoic acid 
• 956-02-5 4'-chlorochalcone 
• 5443-49-2 α-bromocinnamaldehyde 
• 77609-12-2 2-(3-(4-chlorophenyl)-3-oxo-1-phenylpropyl)malononitrile 

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.

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

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.