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Upstream product

• 614-47-1 1,3-diphenyl-propen-3-one 
• 109-77-3 malononitrile 
• 2700-22-3 Benzylidenemalononitrile 
• 532-27-4 1-chloroacetophenone 
• 98-86-2 acetophenone 
• 94-41-7 benzalacetophenone 
• 614-20-0 3-oxo-3-phenylpropionic acid 
• 5443-49-2 α-bromocinnamaldehyde 
• 62940-90-3 2-(3-oxo-1,3-diphenylpropyl)malononitrile 
• 1450991-93-1 2-bromo-3-(3-chlorophenyl)acrylaldehyde 
• 100-52-7 benzaldehyde 

Relevant academic research and scientific papers

Highly enantioselective Michael addition of malononitrile to α,β-unsaturated ketones

The highly enantioselective Michael addition of malononitrile to acyclic and cyclic α,β-unsaturated ketones has been developed. The Michael reaction catalyzed by a primary amine derived from quinidine proceeded smoothly and provided the desired adducts with excellent enantioselectivities (83-97% ee). This journal is The Royal Society of Chemistry.

Organocatalytic enantioselective conjugate additions to enones

Conjugate addition reactions of a wide range of nucleophilic enol species with enones, catalyzed by a cinchona alkaloid derived thiourea organocatalyst, have been developed with attending good yields and high enantioselectivities under a mild reaction con

The asymmetric addition of malononitrile to α,β-unsaturated ketones catalyzed by RuCl2[(R,R)-DPEN](PPh3)2 as the precatalyst

Non-borohydride ruthenium complex, RuCl2[(R,R)-DPEN](PPh 3)2 (1f), was demonstrated to catalyze asymmetric Michael addition of malononitrile to acyclic enones with weak bases. Michael addition of malononitrile to chalcone

Importance of chiral phase-transfer catalysts with dual functions in obtaining high enantioselectivity in the Michael reaction of malonates and chalcone derivatives

(Chemical Equation Presented) Highly enantioselective Michael addition of diethyl malonate to chalcone derivatives has been achieved under mild phase-transfer conditions by the successful utilization of N-spiro C 2-symmetric chiral quaternary a

Functionalised diimidazolium salts: The anion effect on the catalytic ability

The catalytic ability of some functionalised diimidazolium ionic liquids was tested using the Michael addition of malononitrile to t-chalcone as probe reaction. Diimidazolium salts characterized by the presence of 1-(1-imidazolylmethyl)-3,5-di-[1-(3-octylimidazolylmethyl)]benzene cation and differing in the anion structure were used. Both mono- and dianions were employed and among these some chiral anions generally used as organocatalysts were taken into account. Data collected were analysed both as function of ionic liquids structure and basicity, evaluated using the Hammett basicity function. Although the use of chiral anions did not allow performing a stereochemical control of the reaction, data collected demonstrate the high catalytic ability of the functionalised salts. Indeed, high conversions and yields were obtained under mild conditions and in significantly shorter reaction times with respect to the ones so far reported for this reaction.

Asymmetric synthesis of activated cyclopropanes catalyzed by cinchonidine as a chiral Br?nsted base

Cinchonidine catalyzed the cyclopropanation reaction between chloromethyl ketones and β-substituted methylidenemalononitriles to give trans-cyclopropanes with enantioselectivity up to 82% ee. Experimental evidence suggests that cinchonidine functions as a

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.

A complementary pair of enantioselective switchable organocatalysts

A pair of enantioselective switchable bifunctional catalysts are shown to promote a range of conjugate addition reactions in up to 95:5 e.r. and 95% conversion. Each catalyst can be switched OFF using conditions that switch the other catalyst ON. Catalyst

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