748807-16-1Relevant articles and documents
Direct asymmetric organocatalytic Michael reactions of α,α- disubstituted aldehydes with β-nitrostyrenes for the synthesis of quaternary carbon-containing products
Mase, Nobuyuki,Thayumanavan, Rajeswari,Tanaka, Fujie,Barbas III, Carlos F.
, p. 2527 - 2530 (2004)
(Matrix Presented) Direct asymmetric catalytic Michael reactions have been performed using chiral-amine/acid bifunctional catalysts. Performed with 0.3 equiv of (S)-(+)-1-(2-pyrrolidinylmethyl)pyrrolidine and 0.3 equiv of trifluoroacetic acid as the catal
Unmodified Primary Amine Organocatalysts for Asymmetric Michael Reactions in Aqueous Media
Rogozińska-Szymczak, Maria,Mlynarski, Jacek
, p. 6047 - 6051 (2015)
The organocatalytic asymmetric Michael addition of aldehydes to a nitro olefin in aqueous organic solvents catalysed by a broad range of simple primary amines and amino alcohols is reported. In particular, the use of (S,S)-diphenylethylenediamine, which is the chiral backbone of various organocatalysts, gave addition products in good yields and with good to high enantioselectivities (45-96% ee). Remarkably high enantioselectivities were observed for the demanding conjugate addition of α,α-disubstituted aldehydes to nitrostyrene (96-98% ee) in aqueous organic solvent mixtures.
Asymmetric 1,4-Michael Addition in Aqueous Medium Using Hydrophobic Chiral Organocatalysts
Mahato, Chandan K.,Mukherjee, Sayan,Kundu, Mrinalkanti,Vallapure, Virbhadra P.,Pramanik, Animesh
, p. 5213 - 5226 (2021/05/05)
Organic transformations exclusively in water as an environmentally friendly and safe medium have drawn significant interest in the recent years. Moreover, transition metal-free synthesis of enantiopure molecules in water will have a great deal of attentio
Natural eutectogels: Sustainable catalytic systems for C-C bond formation reactions
D'Anna, Francesca,Meli, Alessandro,Ramón, Diego J.,Rizzo, Carla,Saavedra, Beatriz
supporting information, p. 6555 - 6565 (2021/09/10)
Natural eutectogels were prepared by combining the properties of amino acids with the ones of deep eutectic solvents. The soft materials obtained were fully characterised by determining the gel-sol transition temperatures and analysing the mechanical and
Asymmetric michael addition of isobutyraldehyde to nitroolefins using an ?,?-Diphenyl-(S)-prolinol-derived chiral diamine catalyst
Han, Wei,Oriyama, Takeshi
supporting information, p. 988 - 992 (2020/09/22)
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
Enantioselective Michael Addition of Aldehydes to β-Nitrostyrenes Catalyzed by (S)-N-(D-Prolyl)-1-triflicamido-3-phenylpropan-2-amine
Gorde, Amol B.,Ramapanicker, Ramesh
, p. 4745 - 4751 (2019/08/02)
A new organocatalyst for the asymmetric Michael addition reaction of aldehydes with β-nitrostyrenes is developed by coupling D-proline with (S)-1-triflicamido-3-phenylpropan-2-amine, which in turn is prepared from L-phenylalaninol. The Michael addition pr
Phosphinoyl-aziridines as a new class of chiral catalysts for enantioselective Michael addition
Wujkowska, Zuzanna,Zawisza, Anna,Le?niak, Stanis?aw,Rachwalski, Micha?
, p. 230 - 235 (2018/12/05)
A series of new optically pure phosphine oxides containing chiral aziridine subunit were synthesized in good yields and applied as organocatalysts in asymmetric Michael reaction of various aliphatic aldehydes with β-nitrostyrene. The corresponding organoc
D -Prolyl-2-(trifluoromethylsulfonamidopropyl)pyrrolidine: An Organocatalyst for Asymmetric Michael Addition of Aldehydes to β-Nitroalkenes at Ambient Conditions
Gorde, Amol B.,Ramapanicker, Ramesh
, p. 1523 - 1533 (2019/02/07)
Four 2-(trifluoromethylsulfonamidoalkyl)pyrrolidines and their d-prolinamides were prepared and screened as organocatalysts for the Michael addition reaction of aldehydes with β-nitroalkenes at rt and without the use of additives. d-Prolyl-2-(trifluoromet
Asymmetric Michael reaction between aldehydes and nitroalkanes promoted by pyrrolidine-containing C2-symmetric organocatalysts
Bykova,Kostenko,Kucherenko,Zlotin
, p. 1402 - 1406 (2019/08/12)
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
Design, synthesis and application of chiral tetraoxacalix[2]arene[2]triazine-based organocatalysts in asymmetric Michael addition reactions
Genc, Hayriye Nevin,Ozgun, Ummu,Sirit, Abdulkadir
, p. 293 - 300 (2019/02/07)
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