1198362-06-9

Upstream product

• 15241-32-4 1-methoxy-2-(2-nitrovinyl)benzene 
• 78-84-2 isobutyraldehyde 
• 3316-24-3 1-methoxy-2-((E)-2-nitrovinyl)benzene 

Relevant academic research and scientific papers

Design, synthesis and application of chiral tetraoxacalix[2]arene[2]triazine-based organocatalysts in asymmetric Michael addition reactions

A novel type of oxacalix[2]arene[2]triazine-based organocatalysts for asymmetric Michael reactions are reported for the first time. Chiral subunits were attached to the heteroatom-bridged calixaromatic platform by a reaction of (R)- and (S)-1-aminotetrali

Asymmetric michael addition of isobutyraldehyde to nitroolefins using an ?,?-Diphenyl-(S)-prolinol-derived chiral diamine catalyst

The enantioselective Michael addition of isobutyraldehyde to nitroolefin analogs was achieved by utilizing an ?,?-diphenyl(S)-prolinol-derived chiral diamine catalyst 1b. In this protocol, catalyst and additive loadings were reduced to 5 mol% respectively

Asymmetric Michael reaction between aldehydes and nitroalkanes promoted by pyrrolidine-containing C2-symmetric organocatalysts

Bifunctional C2-symmetric organocatalysts derived from chiral 1,2-diaminoethanes and (S)-2-aminomethylpyrrolidine were fi rst used for promoting the asymmetric Michael addition of aliphatic aldehydes to nitroalkenes. The synthesized enantioenri

Chiral Primary Amine-Squaramide Catalyzed Highly Enantioselective Michael Addition of Isobutyraldehyde to Nitroolefins

Chiral primary amine-squaramides have not been extensively studied to date in the field of organocatalysis. In this paper, novel chiral squaramides derived from natural product stevioside were developed. Both enantiomers of a series of γ-nitroaldehydes we

Asymmetric Michael addition organocatalyzed by α,β-dipeptides under solvent-free reaction conditions

The application of six novel α,β-dipeptides as chiral organocatalysts in the asymmetric Michael addition reaction between enolizable aldehydes and N-arylmaleimides or nitroolefins is described. With N-arylmaleimides as substrates, the best results were achieved with dipeptide 2 as a catalyst in the presence of aq. NaOH. Whereas dipeptides 4 and 6 in conjunction with 4-dimethylaminopyridine (DMAP) and thiourea as a hydrogen bond donor proved to be highly efficient organocatalytic systems in the enantioselective reaction between isobutyraldehyde and various nitroolefins.

In search of diamine analogs of the α,α-diphenyl prolinol privileged chiral organocatalyst. Synthesis of diamine derivatives of α,α-diphenyl-(S)-prolinol and their application as organocatalysts in the asymmetric Michael and Mannich reactions

This paper describes improved reaction conditions for the substitution of the hydroxyl group in (S)-diphenyl(pyrrolidin-2-yl)methanol by the azide group, which was then reduced to the diamine derivative. We examined two protecting groups (N-Bn and N-Boc) on the pyrrolidine nitrogen in order to functionalize the primary amino group into various amide, alkylated amine, sulfonamide, thiourea and triazole derivatives. Notably, carefully controlled conditions were required to generate the desired derivatives from the sterically hindered benzhydrylamine moiety. Unexpectedly, upon removal of the N-protecting group in derivatives containing electrophilic polar double bonds (C=S, C=O) cyclization took place, affording products such as amidines. The target compounds were evaluated as bifunctional organocatalysts in the asymmetric Michael and Mannich addition reactions. (S)-2-(Azidodiphenylmethyl)pyrrolidine (S)-7 was identified as the most efficient organocatalyst among the various diamine derivatives of α,α-diphenyl-(S)-prolinol prepared in this work.

Calixarene-based highly efficient primary amine-thiourea organocatalysts for asymmetric Michael addition of aldehydes to nitrostyrenes

The synthesis of calix[4]arene-based chiral bifunctional primary amine-thiourea catalysts has been described from p-tert-butylcalix[4]arene for the first time. The calix[4]arene-based catalysts were successfully applied to promote Michael addition of alde

Highly enantioselective Michael additions of isobutyraldehyde to nitroalkenes promoted by amphiphilic bifunctional primary amine-thioureas in organic or aqueous medium

A novel class of chiral amphiphilic bifunctional thioureas based on a beyerane scaffold and each containing a primary amino group were designed and synthesized from the readily available natural product isosteviol. The thioureas were shown to be effective

ORGANOCATALYST

The present invention provides an organocatalyst of formula (I), wherein R1 is —H, —OH, —O—Si(R4)(R5)(R6) or C1-6alkoxy, in which R4, R5 and R6 are identical or differ

Highly enantioselective Michael addition of aldehy des to nitroolefins catalyzed by primary amine thiourea organocatalysts

Asymmetric Michael addition reactions of aldehydes to nitroolefins have been successfully initiated by a series of primary amine thiourea bifunctional catalysts, with high enantioselectivities (90-98% ee) and excellent yields (80-96%).The privileged quini