479499-52-0

Upstream product

• 66646-88-6 (E)-N-benzylideneglycine methyl ester 
• 292638-85-8 acrylic acid methyl ester 
• 66646-88-6 methyl 2-(benzylideneamino)acetate 
• 100-52-7 benzaldehyde 

Relevant academic research and scientific papers

A class of α-amino acids-derived multifunctional amidophosphane precatalysts: application to the highly enantio- and diastereoselective silver(I)-catalyzed 1,3-dipolar cycloaddition reaction

A class of multifunctional amidophosphanes derived from chiral α-amino acids have been developed with two amide bonds, a tertiary amine and a phosphine. In combination with Ag(I) salts, these amidophosphanes have been demonstrated as highly efficient multifunctional catalysts in the asymmetric 1,3-dipolar cycloaddition of azomethine ylides as well as the three-component reaction of the α-iminoesters in situ generated. Under optimal conditions, highly functionalized endo-8 pyrrolidines were obtained with good to excellent yields (up to 99% yield) and enantioselectivities (up to 98% ee).

Ag(I)/CAAA-Amidphos Complex Catalyzed Asymmetric 1,3-Dipolar Cycloaddition of Acrylates for the Formal Synthesis of (+)-Ibophyllidine

In this work, we introduced a multifunctional Ag(I)/CAAA-amidphos complex catalyzed asymmetric 1,3-dipolar cycloaddition of acrylates with α-imino esters, affording a series of 2,4,5-trisubstituted endo -pyrrolidines in good yields (up to 97%) with high enantioselectivities (up to 98% ee). Meanwhile, the catalytic system was also applied in the three-component one-pot reaction of α-imino esters formed in situ under the action of N,N ′-diisopropylcarbodiimide. In addition, the gram-scale reaction was realized for the formal synthesis of (+)-ibophyllidine in eight steps.

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.

Switching Diastereoselectivity in Catalytic Enantioselective (3+2) Cycloadditions of Azomethine Ylides Promoted by Metal Salts and Privileged Segphos-Derived Ligands

Catalytic enantioselective 1,3-dipolar cycloaddition between imino esters and electrophilic alkenes, employing chiral metal complexes derived from copper(I) and silver(I) salts and (S)-DM-or (S)-DTBM-Segphos as ligands produces diastereodivergently exo-or

A Chiral Secondary Amine-Amidophosphane Precatalyst for Silver-Catalyzed Asymmetric 1,3-Dipolar Cycloaddition Reactions

A class of multifunctional amidophosphanes derived from chiral 1,2-diphenylethylenediamines and natural α-amino acids has been developed. Among these, in combination with silver(I) salts, a chiral secondary amine-amidophosphane precatalyst has been demonstrated as being a highly efficient multifunctional precatalyst in the asymmetric 1,3-dipolar cycloaddition of azomethine ylides, including a series of heterocyclic, aliphatic, and 2-substituted azomethine ylides, and aromatic α,β-unsaturated aldehyde derived imino esters with different electron-deficient alkenes, as well as the three-component reaction of α-imino esters generated in situ by using N, N ′-diisopropylcarbodiimide as dehydrating agent. Under optimal conditions, highly functionalized endo -adducts were obtained in high to excellent yields (up to 99% yield) and enantioselectivities (up to >99.9% ee).

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).

Development of chiral metal amides as highly reactive catalysts for asymmetric [3 + 2] cycloadditions

Highly efficient catalytic asymmetric [3 + 2] cycloadditions using a chiral copper amide are reported. Compared with the chiral CuOTf/Et3 N system, the CuHMDS system showed higher reactivity, and the desired reactions proceeded in high yields a

Asymmetric [3+2] cycloaddition of azomethine ylides catalyzed by silver(I) triflate with a chiral bipyrrolidine-derived phosphine ligand

Two novel chiral bipyrrolidine-derived phosphine ligands L1 and L2 were synthesized. The AgOTf + L1 protocol catalyzes the asymmetric [3+2] cycloaddition of azomethine ylides with alkenes to give highly substituted pyrrolidines in good yields (up to 90%) with moderate to high diastereoselectivities (up to >19:1 dr) and enantioselectivities (up to 76%). Georg Thieme Verlag Stuttgart.New York.

Switching the stereoselectivity: (Fullero)Pyrrolidines "a la Carte"

Stereodivergent syntheses of cis/trans pyrrolidino[3,4:1,2]fullerenes and endo/exo pyrrolidines are reported with high enantioselectivity levels. Fullerenes are revealed as a useful benchmark to develop suitable catalysts to control the stereochemical out

Chiral silver amide catalyst for the [3+2] cycloaddition of α-amino esters to olefins

Silver lining: Highly exo-selective asymmetric [3+2]cycloaddition of α-amino ester Schiff bases with activated olefins proceeds in the presence of AgHMDS/1. The α-amino ester Schiff bases including those derived from aliphatic imines successfully reacted