1350897-04-9Relevant articles and documents
Asymmetric Michael addition organocatalyzed by α,β-dipeptides under solvent-free reaction conditions
Avila-Ortiz, C. Gabriela,Lenin, Diaz-Corona,Erika, Jiménez-González,Juaristi, Eusebio
, (2017)
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.
Organocatalytic enantioselective conjugate addition of aldehydes to maleimides in deep eutectic solvents
Flores-Ferrándiz, Jesús,Chinchilla, Rafael
, p. 302 - 306 (2017/02/18)
The conjugate enantioselective addition of aldehydes, mainly α,α-disubstituted, to maleimides leading to enantioenriched succinimides, has been achieved in recyclable deep eutectic solvents at room temperature. Enantiomerically pure carbamate-monoprotecte
Stereoselective conjugate addition of carbonyl compounds to maleimides using a diaminomethyleneindenedione organocatalyst
Nakashima, Kosuke,Kawada, Masahiro,Hirashima, Shin-ichi,Kosugi, Ayako,Kato, Mana,Yoshida, Akihiro,Koseki, Yuji,Miura, Tsuyoshi
, p. 888 - 895 (2016/09/02)
A diaminomethyleneindenedione motif can serve as an excellent double hydrogen bonding donor. Bifunctional chiral primary amine 3 bearing a diaminomethyleneindenedione motif is an excellent organocatalyst to promote the asymmetric conjugate additions of va
Solvent-induced reversal of enantioselectivity in the synthesis of succinimides by the addition of aldehydes to maleimides catalysed by carbamate-monoprotected 1,2-diamines
Flores-Ferrndiz, Jess,Fiser, Bla,Gmez-Bengoa, Enrique,Chinchilla, Rafael
, p. 1218 - 1225 (2015/03/04)
A simple change in the polarity of the solvent allows both enantiomers of substituted succinimides to be obtained in the enantioselective conjugate addition reaction of aldehydes, mainly disubstituted, to maleimides catalysed by chiral carbamate-monoprote
Solvent-dependent enantioswitching in the Michael addition of α,α-disubstituted aldehydes to maleimides organocatalyzed by mono-N-Boc-protected cyclohexa-1,2-diamines
Flores-Ferrándiz, Jesús,Chinchilla, Rafael
, p. 1091 - 1094 (2014/10/15)
Enantiomerically pure mono-N-Boc-protected trans-cyclohexa-1,2-diamines are used as organocatalysts for the enantioselective conjugate addition of α,α-disubstituted aldehydes to maleimides. Using a single enantiomer of the organocatalyst, both enantiomeri
An asymmetric Michael addition of α,α-disubstituted aldehydes to maleimides leading to a one-pot enantioselective synthesis of lactones catalyzed by amino acids
Kokotos, Christoforos G.
supporting information, p. 2406 - 2409 (2013/06/27)
A cheap and fast construction of both enantiomers of substituted succinimides is reported. α- or β-amino acids, such as β-phenylalanine and α-tert-butyl aspartate, were found to be efficient organocatalysts for the reaction between α,α-disubstituted aldeh
Calixarene-based chiral primary amine thiourea promoted highly enantioselective asymmetric Michael reactions of α,α-disubstituted aldehydes with maleimides
Durmaz, Mustafa,Sirit, Abdulkadir
, p. 1443 - 1448 (2013/12/04)
Calix[4]arene based chiral bifunctional thiourea-primary amines have been shown to act as effective catalysts for the Michael addition of aldehydes to maleimides for the first time. The corresponding adducts were generally obtained preferentially in (R)-
Enantioselective Michael addition of aldehydes to maleimides organocatalysed by chiral 1,2-diamines: An experimental and theoretical study
Avila, Angel,Chinchilla, Rafael,Gomez-Bengoa, Enrique,Najera, Carmen
, p. 1531 - 1535 (2013/12/04)
Simple and commercially available chiral 1,2-diamines were used as organocatalysts for the enantioselective conjugate addition of aldehydes, including α,α-disubstituted, to maleimides. The reaction was carried out in the presence of hexanedioic acid as an
Enantioselective Michael addition of α,α-disubstituted aldehydes to maleimides organocatalyzed by chiral primary amine-guanidines
Avila, Angel,Chinchilla, Rafael,Nájera, Carmen
, p. 1625 - 1627 (2013/02/22)
New primary amine-guanidines derived from the monoguanylation of (1S,2S)- and (1R,2R)-cyclohexane-1,2-diamine have been prepared and used as chiral organocatalysts for the enantioselective conjugate addition of α,α-disubstituted aldehydes to maleimides. T
Asymmetric Michael reactions of α,α-disubstituted aldehydes with maleimides using a primary amine thiourea organocatalyst
Miura, Tsuyoshi,Masuda, Akira,Ina, Mariko,Nakashima, Kosuke,Nishida, Shohei,Tada, Norihiro,Itoh, Akichika
experimental part, p. 1605 - 1609 (2011/12/16)
Primary amine thiourea organocatalyst 8 was used to promote Michael additions of bulky α,α-disubstituted aldehydes, such as isobutyraldehyde with maleimides to afford the corresponding adducts in high to excellent yields and with up to 91% ee. Copyright