359876-02-1

Upstream product

• 917-54-4 methyllithium 
• 182360-64-1 2-((S)-2-Chlorocarbonyl-1-phenyl-ethyl)-malonic acid dimethyl ester 
• 67-56-1 methanol 
• 844885-47-8 (S)-2-cyano-5-oxo-3-phenylhexanoic acid methyl ester 
• 182511-39-3 (S)-2-(3-oxo-1,3-diphenyl-propyl)-malonic acid diethyl ester 
• 1896-62-4 (E)-benzalacetone 
• 108-59-8 malonic acid dimethyl ester 
• 122-57-6 1-Phenylbut-1-en-3-one 
• 182360-62-9 (S)-2-phenyl-1,1,3-propanetricarboxylic acid 1,1-dimethyl ester 
• 164931-80-0 (S)-(3-oxo-1,3-diphenyl-propyl)-malonic acid dimethyl ester 
• 5292-53-5 diethyl benzalmalonate 
• 6626-84-2 dimethyl 2-benzylidenepropanedioate 

Downstream Products

• 108056-65-1 methyl (S)-(-)-5-oxo-3-phenylhexanoate 
• 108056-64-0 (S)-5-oxo-3-phenylhexanoic acid 

Relevant academic research and scientific papers

Solvent-Free Enantioselective Michael Reactions Catalyzed by a Calixarene-Based Primary Amine Thiourea

An upper-rim functionalized calix[4]arene-based thiourea installed onto the (R,R)-1,2-cyclohexanediamine scaffold was synthesized with a view to investigate its catalytic ability in enantioselective Michael additions. The reactions were found to conveniently proceed under solvent-free conditions, observing good to high enantioselectivities. From this preliminary study, the calix[4]arene unit is likely to play a role in affecting the conversion and to a lesser extent to the stereochemical outcome of the reactions through van der Waals contacts and C-H···π interactions with the substrates.

Enantioselective Michael Addition of Malonates to Chalcone Derivatives Catalyzed by Dipeptide-derived Multifunctional Phosphonium Salts

Highly enantioselective Michael addition of malonates to enones catalyzed by dipeptide-derived multifunctional phosphonium salts has been developed. The newly established catalytic system was characterized with its wide substrate scope featured with aliphatic aldehyde-derived enones and substituted malonates. The gram scale-up synthesis of adducts can also be successfully achieved under optimal conditions with both excellent yield and enantioselectivity.

Solvent-free asymmetric conjugate addition of malonates to enones using a diaminomethylenemalononitrile organocatalyst

Diaminomethylenemalononitrile organocatalyst 1 efficiently promotes the asymmetric conjugate addition of malonates to α,β-unsaturated ketones to afford the corresponding addition products in high to excellent yields with up to 98% ee.

Hydroxy-L-prolines as asymmetric catalysts for aldol, Michael addition and Mannich reactions

The hydroxyprolines (Hyps) 2-6 are tested as organocatalysts for aldol, Michael additions, and Mannich reactions. The results are compared with the well-known analogous L-proline (1).The effect of the additional hydroxyl group and chiral center was invest

An efficient organocatalytic method for highly enantioselective michael addition of malonates to enones catalyzed by readily accessible primary amine-thiourea

A practical and highly enantioselective Michael addition of malonates to enones catalyzed by simple and readily available bifunctional primary amine-thiourea derived from 1,2-diaminocyclohexane is reported. The addition of weak acids and elevated temperature (ca. 50 °C) improved the efficiency of the Michael reaction. This approach enables the efficient synthesis of 1,5-ketoesters with good yields, excellent enantioselectivities (up to 99% ee), and low loading (0.5-5 mol %) of simple chiral primary amine-thiourea catalysts, and is applicable in multigram scale synthesis.

Organocatalytic enantioselective Michael additions of malonates to 2-cyclopentenone

The Michael reaction of a dialkyl malonate with a cyclic enone using a chiral diamine-acid combination catalyst gave the desired Michael adduct in high yield with excellent enantiomeric excess in a protic solvent such as methanol and ethanol. The methanol

Novel guanidinyl pyrrolidine salt-based bifunctional organocatalysts: application in asymmetric conjugate addition of malonates to enones

Novel guanidinyl pyrrolidine salts are useful bifunctional organocatalysts for the asymmetric addition of malonates to enones. These organocatalysts are effective under a wide range of reaction conditions and afford products in high yield and enantioselec

Enantioselective organocatalytic Michael addition of malonates to α,/β-unsaturated ketones

(Chemical Equation Presented) A novel type of primary amine thiourea organocatalysts derived from 1,2-diaminocyclohexane and 9-amino (9-deoxy) cinchona alkaloid was developed into asymmetric Michael addition of malonates to enones. A series of cyclic and

A general organocatalytic enantioselective malonate addition to α,β-unsaturated enones

A general enantioselective organocatalytic conjugate addition procedure of a variety of malonates to α,β-unsaturated enone systems is presented. The reaction is efficiently catalysed by the pyrrolidinyl tetrazole catalyst 1. Cyclic, acyclic and aromatic e

Organocatalyzed highly enantioselective michael additions of malonates to enones by using novel primary-secondary diamine catalysts

A novel primary-secondary diamine catalyst readily available from primary amino acids in three steps for the highly enantioselective Michael additions of malonates to α,β-unsaturated ketones was reported. The Michael reaction of dimethyl malonate with benzylideneacetone was selected as a model reaction for catalyst evaluation. The length of the alkyl chain is found to influence the catalytic abilities of the catalysts and the n-propylated catalyst gave the highest yield and ee value. The addition of a series of malonates to enone performed under the optimized conditions is found to be sensitive to the steric hinderance on the malonates. Heterocyclic furan enone is found to perform well to give the desired product in 92% yield and 99% ee, while no decrease in yield and ee value is observed for sterically hindered enone.