75516-81-3

Upstream product

• 40216-71-5 methyl 2-(benzylideneamino)propanoate 
• 23055-10-9 1,4-dimethyl but-2-enedioate 
• 119993-27-0 dimethyl N-benzylidene-3-methoxycarbonyl-2-methylglutamate 
• 100-52-7 benzaldehyde 
• 120328-90-7 methyl (E)-N-benzylidenealaninate 
• 624-49-7 dimethylfumarate 
• 67628-21-1 methyl (3aRS,4SR,6RS,6aSR)-4-methyl-1,3-dioxo-6-phenylhexahydro-1H-furo[3,4-c]pyrrole-4-carboxylate 
• 624-48-6 dimethyl cis-but-2-ene-1,4-dioate 
• 53933-42-9 2-(benzylidene-amino)-propionic acid methyl ester 

Relevant academic research and scientific papers

CHIRAL 1,2-DIAMINOCYCLOHEXANE-α-AMINO ACID-DERIVED AMIDPHOS/Ag(I)-CATALYZED DIVERGENT ENANTIOSELECTIVE 1,3-DIPOLAR CYCLOADDITION of AZOMETHINE YLIDES

A series of chiral 1,2-diaminocyclohexane-α-amino acid-derived amidophosphanes in combination with silver(I) salts, have been developed to cooperatively catalyze the azomethine ylides-involved 1,3-dipolar cycloaddition with different electron-deficient alkenes. Among these, the (1S,2S)-1,2-cyclohexanediamine-L-tert-leucine-derived amidphos/Ag(I) has been demonstrated as being a highly efficient catalytic system in the cis-1,2-disubstituted electron-deficient olefins-involved 1,3-dipolar cycloaddition of azomethine ylides, including a series of aromatic, heteroaromatic, aliphatic, and 2-substituted azomethine ylides, affording various fully substituted pyrrolidines in high to excellent yields (up to 97% yield) and enantioselectivities (up to 97% ee). Interestingly, the (1R,2R)-1,2-cyclohexanediamine-L-tert-leucine-derived amidphos/Ag(I) can efficiently catalyze terminal electron-deficient olefin-involved 1,3-dipolar cycloaddition, giving a series of 2,4,5-tri-substituted pyrrolidines with up to 92% yield and 92% ee.

A novel multifunctional phosphonates/amide ligand catalyst and its synthesis and use

The invention discloses a novel multifunctional phosphine/amide ligand catalyst as well as a synthesis method and an application thereof. The catalyst has a structure as shown in a formula (I) or a formula (II). The molecular structure of the catalyst is scientifically designed, so that the catalyst can be well combined with metal Lewis acid to form a new catalytic system, namely a bronsted/Lewis alkali-Lewis acid system, so that the system activates a nucleophilic reagent and an electrophilic agent which participate in reaction at the same time so as to jointly control a transition state in the reaction, a corresponding chiral environment can be effectively generated, more space can be provided for modifying the structure and changing the metal Lewis acid, so that high selectivity is obtained. The formula (I) and the formula (II) are as shown in the specification, wherein in the formula (I), R represents H, Me, Bn, Ph, iPr or tBu.

l-tert-Leucine-Derived AmidPhos-Silver(I) Chiral Complexes for the Asymmetric [3+2] Cycloaddition of Azomethine Ylides

The l-tert-leucine-derived AmidPhos/silver(I) catalytic system has been developed for the asymmetric [3+2] cycloaddition of azomethine ylides with electronic-deficient alkenes with or without Et3N. Under optimal conditions, highly functionalized endo-4-pyrrolidines were obtained with modest to high yields (up to 99% yield) and enantioselectivities (up to 98% ee).

Ag2CO3/CA-AA-amidphos multifunctional catalysis in the enantioselective 1,3-dipolar cycloaddition of azomethine ylides

The new Ag2CO3/CA-AA-amidphos complexes have been demonstrated as highly efficient multifunctional catalysts in the asymmetric 1,3-dipolar cycloaddition of azomethine ylides. Under optimal conditions, highly functionalized endo-4 pyrrolidines were obtained with excellent yields (up to 99% yield) and enantioselectivities (up to 96% ee).

X=Y-ZH SYSTEMS AS POTENTIAL 1,3-DIPOLES. PART 15. AMINE GENERATED AZAALLYL ANIONS VERSUS METALLO-1,3-DIPOLES IN CYCLOADDITIONS OF α-AMINO ACID ESTERS. FACILE REGIO- AND STEREO-SPECIFIC FORMATION OF PYRROLIDINES.

Kinetic studies of the deprotonation of arylidine imines of alanine and phenylglycine esters by tertiary amines and pyridine and cycloaddition of the resultant 4?-azaallyl anions to N-phenylmaleimide show the expected dependance on the p-substituent in th

Lithium Bromide/Triethylamine Induced Cycloaddition of N-Alkylidene 2-Amino Esters and Amides to Electron-Deficient Olefins with High Regio- and Stereoselectivity

The imines of 2-amino esters and amides derived from glycine, alanine, and valine are deprotonated by the action of a lithium halide and triethylamine (or DBU).The resulting anionic intermediates undergo highly regio- and stereoselective cycloadditions with a variety of olefins activated by carbonyl-type substituents to produce stereochemically defined derivatives of proline esters or amides.The scope and limitations of this novel cycloaddition are discussed.

X=Y-ZH SYSTEMS AS POTENTIAL 1,3-DIPOLES. PART 17. SEQUENTIAL MICHAEL ADDITION-5-ENDO-TRIG CYCLISATION OF ARYLIDENE IMINES OF Α-AMINO ACID ESTERS

Imines of α-amino acid esters undergo regiospecific Michael addition to methyl acrylate or acrylonitrile in good yield in benzene at 25 degC catalysed by benzyltrimethylammonium methoxide (BTAM).The Michael adducts cyclise to a mixture of two stereoisomer

X=Y-ZH SYSTEMS AS POTENTIAL 1,3-DIPOLES. PART 14. BRONSTED AND LEWIS ACID CATALYSIS OF CYCLOADDITIONS OF ARYLIDENE IMINES OF α-AMINO ACID ESTERS

Cycloadditions of arylidene imines of α-amino acid esters to a range of dipolarophiles show substantial rate enhancements in the presence of Bronsted and Lewis acids.For Bronsted acids the rate is related to the pKa of the acid and cycloadditio

X=Y-ZH Systems as Potential 1,3-Dipoles. Part 7. Stereochemistry of the Cycloaddition of Imines of α-Amino Acid Esters to Fumarate and Maleate Esters

Aryl imines of α-amino acid esters undergo 1,3-dipolar cycloadditions with maleate and fumarate esters in quantitative yield when heated in boiling toluene to give mixtures of mainly two pyrrolidines.The major isomer in each case arises from cycloaddition

X=Y-ZH SYSTEMS AS POTENTIAL 1,3-DIPOLES. THE STEREOCHEMISTRY AND REGIOCHEMISTRY OF CYCLOADDITION REACTIONS OF IMINES OF α-AMINO-ACID ESTERS.

The stereochemistry and regiochemistry of cycloadditions of α-amino acid ester imines is dependent both on imine structure and on the reactivity of the dipolarophile.Phenylglycine imines undergo competing dipole stereomutation and cycloaddition with some dipolarophiles.