409095-87-0Relevant academic research and scientific papers
Anti-selective direct asymmetric Mannich reactions catalyzed by axially chiral amino sulfonamide as an organocatalyst
Kano, Taichi,Yamaguchi, Yukako,Tokuda, Osamu,Maruoka, Keiji
, p. 16408 - 16409 (2005)
A direct asymmetric Mannich reaction using a novel axially chiral amino trifluoromethanesulfonamide (S)-3 has been developed in highly anti-selective and enantioselective manners. Thus, in the presence of a catalytic amount of (S)-3, the reactions between
Enantioselective anti-Mannich reaction catalyzed by modularly designed organocatalysts
Konda, Swapna,Zhao, John C.-G.
, p. 6166 - 6172 (2018/09/12)
A highly stereoselective method for achieving the anti-Mannich reaction of aldehydes and ketones with ethyl (4-methoxyphenylimino)acetate was realized using the modularly designed organocatalysts (MDOs) self-assembled from cinchona alkaloid derivatives an
Asymmetric anti-Mannich reactions in continuous flow
Martin-Rapun, Rafael,Sayalero, Sonia,Pericas, Miquel A.
supporting information, p. 3295 - 3301 (2013/12/04)
A polystyrene-supported, pyrrolidine-based catalyst depicting very high activity and excellent stereoselectivity in the anti-Mannich reaction of aldehydes and ketones has been developed. The very robust, immobilized catalyst has been successfully used in
Highly active organocatalysts for asymmetric anti-mannich reactions
Martín-Rapún, Rafael,Fan, Xinyuan,Sayalero, Sonia,Bahramnejad, Mahboubeh,Cuevas, Félix,Pericàs, Miquel A.
supporting information; experimental part, p. 8780 - 8783 (2011/09/15)
Lighten the load! A family of enantiopure 4-oxy-substituted 3-aminopyrrolidines arising from the enantioselective ring-opening of meso-3-pyrroline oxide have been developed as catalysts for the asymmetric, anti-selective Mannich reaction (see scheme; PMP=
A designer axially chiral amino sulfonamide as an efficient organocatalyst for direct asymmetric anti/-selective mannich reactions and syw-selective cross-aldol reactions
Kano, Taichi,Yamaguchi, Yukako,Maruoka, Keiji
supporting information; experimental part, p. 6678 - 6687 (2010/02/28)
A direct asymmetric Mannich reaction using a novel axially chiral amino sulfonamide (S)-3 that is highly anti- and enantioselective has been developed. For instance, in the presence of a catalytic amount of (S)-3, the reactions between aldehydes and a-imino esters proceeded smoothly to give anti Mannich products with a significantly higher antilsyn ratio and enantioselectivity than previously possible. By utilizing N-Boc-protected aro-matic imines instead of a-imino esters, the synthetically useful Boc protecting group and various aromatic or heteroaromatic substituents were installed into the anti Mannich products and consequently the substrate scope of the anri'-selective Mannich reaction and the synthetic utility of the anti Mannich products have been expanded. The axially chiral amino sulfonamide (S)-3 has also been successfully applied to asymmetric direct cross-aldol reaction between two different aldehydes. The catalyst (S)-3 has the advantage of giving mainly syn products, whereas proline shows the opposite anti selectivity.
12 MEMBERED-RING MACROLACTAM DERIVATIVES
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Page/Page column 21-22, (2009/01/24)
There provided a 12-membered-ring macrolactam derivative having antitumor activity: A compound represented by Formula (1) or a salt thereof. In this Formula, R1 is a hydrogen atom, a C1-6 alkyl group, a C1-6 alkylcarbonyl
TRANS-3,5-DISUBSTITUTEDPYRROLIDINE: ORGANOCATALYST FOR anti-MANNICH REACTIONS
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Page/Page column 15; 24; 25, (2010/11/27)
A compound of Formula I is disclosed, in which R is a substituent containing a hydrogen bond-forming atom within three atoms from the ring carbon to which the substituent is bonded; X is CH2, O, S or NR1, wherein R1 is a hydrocarbyl group or an amino-protecting group having one to about 18 carbon atoms; R2 is hydrido or a hydrocarbyl group containing one to about twelve carbon atoms; and R3 is hydrido or methyl, but both R2 and R3 are not hydrido when X is CH2 A molecule of Formula I and those in which R2 and R3 can both be hydrido (Formula X) functions as a catalyst in a Mannich reaction to asymmetrically form β-aminoaldehyde or β-aminoketone diastereomeric products having two chiral centers on adjacent carbon atoms and in which the anti-diastereomers are in excess over the syn-diastereomers. Methods for carrying out those syntheses are also disclosed.
Direct asymmetric anti-Mannich-type reactions catalyzed by a designed amino acid
Mitsumori, Susumu,Zhang, Haile,Cheong, Paul Ha-Yeon,Houk,Tanaka, Fujie,Barbas, Carlos F.
, p. 1040 - 1041 (2007/10/03)
The development of catalysts for Mannich-type reactions that afford anti-products with excellent diastereo- and enantioselectivities under mild conditions and low catalyst loadings (1-5 mol %) is reported. Based on principles gained from the study of (S)-
Direct catalytic asymmetric anti-selective Mannich-type reactions
Ibrahem, Ismail,Cordova, Armando
, p. 1760 - 1762 (2008/09/16)
The simple chiral pyrrolidine catalyzed asymmetric anti-selective Mannich-type reaction is presented; the reaction gives the corresponding amino acid derivatives with 10:1->19:1 dr and 97-99% ee. The Royal Society of Chemistry 2006.
A general organocatalyst for direct α-functionalization of aldehydes: Stereoselective C-C, C-N, C-F, C-Br, and C-S bond-forming reactions. Scope and mechanistic insights
Franzen, Johan,Marigo, Mauro,Fielenbach, Doris,Wabnitz, Tobias C.,Kjaersgaard, Anne,Jorgensen, Karl Anker
, p. 18296 - 18304 (2007/10/03)
The development of a general organocatalyst for the α- functionalization of aldehydes, via an enamine intermediate, is presented. Based on optically active α,α-diarylprolinol silyl ethers, the scope and applications of this catalyst for the stereogenic fo
