109012-81-9

Upstream product

• 122-57-6 1-Phenylbut-1-en-3-one 
• 108-59-8 malonic acid dimethyl ester 
• 186581-53-3 diazomethane 
• 4354-90-9 (3-oxo-1-phenyl-butyl)-malonic acid 
• 1896-62-4 (E)-benzalacetone 
• 67-56-1 methanol 
• 124-41-4 sodium methylate 
• 500055-91-4 cyano-2 phenyl-3 oxo-5 hexanoate de methyle 

Downstream Products

• 146497-71-4 methyl 2-hydroxy-4-oxo-6-phenylcyclohex-2-enecarboxylate 
• 4354-90-9 (3-oxo-1-phenyl-butyl)-malonic acid 
• 211818-69-8 methyl(E)-2-methoxycarbonyl-5-methylsulfonyloxyimino-3-phenylhexanoate 

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.

Asymmetric conjugate addition of malonate to α,β-unsaturated ketones in water using a perfluoroalkanesulfonamide organocatalyst

Perfluoroalkanesulfonamide organocatalyst 7 efficiently promotes asymmetric Michael additions of malonates to enones in cyclohexane or water to produce the corresponding addition products with excellent yields and with up to 99% ee.

Asymmetric organocatalytic conjugate addition of malonates to enones using a proline tetrazole catalyst

5-Pyrrolidin-2-yltetrazole performs as a useful organocatalyst for the asymmetric addition of malonates to a range of enones, with good to excellent enantioselectivities. The Royal Society of Chemistry 2006.

Electrochemically induced addition reactions in the absence of solvent and supporting electrolyte

Solvent- and supporting electrolyte-free electrolysis in a two-compartment cell proved to be effective for the direct electroactivation of C-H acid-containing compounds vs. catalytic addition processes. Michael adducts (including quaternary carbon centres

Enantioselective synthesis of 2,4,5-trisubstituted tetrahydropyrans via peptide-catalyzed michael addition followed by Kishi's reductive cyclization

An enantioselective synthesis of 2,4,5-trisubstituted tetrahydropyrans has been achieved in four steps from α,β-unsaturated ketones and dimethyl malonate by peptide-catalyzed asymmetric Michael addition and diastereoselective construction of tetrahydropyr

Helical-Peptide-Catalyzed Enantioselective Michael Addition Reactions and Their Mechanistic Insights

Helical peptide foldamer catalyzed Michael addition reactions of nitroalkane or dialkyl malonate to α,β-unsaturated ketones are reported along with the mechanistic considerations of the enantio-induction. A wide variety of α,β-unsaturated ketones, including β-aryl, β-alkyl enones, and cyclic enones, were found to be catalyzed by the helical peptide to give Michael adducts with high enantioselectivities (up to 99%). On the basis of X-ray crystallographic analysis and depsipeptide study, the amide protons, N(2)-H and N(3)-H, at the N terminus in the α-helical peptide catalyst were crucial for activating Michael donors, while the N-terminal primary amine activated Michael acceptors through the formation of iminium ion intermediates.

A kind of T-leucine derivative of the chiral amine compound and its preparation method and application

The invention discloses a tertiary leucine derived chiral amine compound as well as a preparation method and application thereof. The chiral amine compound contains a tert-butyl group, a primary amine, a secondary amine or a tertiary amine functional group and has the structural formula as shown in the specification; and chiral amine and salts thereof are prepared through simple preparation steps by taking common tert-leucine as the raw material to form the chiral amine compound. The chiral amine and the salts thereof can be used for the asymmetrical Michael additive reaction between alpha, beta-unsaturated ketone and a nucleophilic reagent such as nitrocarbol, malonic ester, substituted oxazolone and the like and the asymmetrical cascade reaction between the alpha, beta-unsaturated ketone and fifth-position unsaturated rhodanine, between fifth-position unsaturated hydantoin and the alpha, beta-unsaturated ketone; and the tertiary leucine derived chiral amine compound has very high catalytic activity and stereoselectivity as well as the highest diastereoselectivity of 30/1 and the highest enantioselectivity of 99%, and is wide in oligomer range.

Asymmetric conjugate addition of malonates to enones using Perfluorobutanesulfonamide organocatalyst

Perfluorobutanesulfonamide organocatalyst 4 efficiently promotes asymmetric conjugate additions of malonates to α,β-unsaturated ketones to afford the corresponding adducts with excellent enantioselectivities (up to 99% ee).

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.

Simple chiral sulfonamide primary amine catalysed highly enantioselective Michael addition of malonates to enones

A chiral sulfonamide primary amine-organocatalysed, highly enantioselective Michael addition of malonates to enones has been developed. This reaction afforded the corresponding products in excellent yields (up to 99%) and excellent enantioselectivity (up