75984-50-8

Upstream product

• 40216-71-5 methyl 2-(benzylideneamino)propanoate 
• 292638-85-8 acrylic acid methyl ester 
• 120328-90-7 methyl (E)-N-benzylidenealaninate 
• 64298-96-0 dimethyl 2-(benzylideneamino)-2-methylglutarate 
• 64298-96-0 dimethyl 2-(benzylideneamino)-2-methylpentanedioate 
• 100-52-7 benzaldehyde 
• 75517-02-1 dimethyl 2-methyl-5-phenylpyrrolidine-2,4-dicarboxylate 

Downstream Products

• 75517-02-1 (2S,4R,5R)-2-Methyl-5-phenyl-pyrrolidine-2,4-dicarboxylic acid dimethyl ester 

Relevant academic research and scientific papers

X=Y-ZH systems as potential 1,3-dipoles. Part 61: Metal exchanged zeolites, silver(I) oxide, Ni(II) and Cu(I) complexes as catalysts for 1,3-dipolar cycloaddition reactions of imines generating proline derivatives

A range of regio- and stereo-selective 1,3-dipolar reactions of imines of α-amino esters, generating polysubstituted prolines, catalysed by silver(I) exchanged zeolites or silver(I) supported on titania, both in combination with DBU, are described. The us

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.

Development of catalytic asymmetric 1,4-addition and [3 + 2] cycloaddition reactions using chiral calcium complexes

Catalytic asymmetric 1,4-addition and [3 + 2] cycloaddition reactions using chiral calcium species prepared from calcium isopropoxide and chiral bisoxazoline ligands have been developed. Glycine Schiff bases reacted with acrylic esters to afford 1,4-addition products, glutamic acid derivatives, in high yields with high enantioselectivities. During the investigation of the 1,4-addition reactions, we unexpectedly found that a [3 + 2] cycloaddition occurred in the reactions with crotonate derivatives, affording substituted pyrrolidine derivatives in high yields with high enantioselectivities. On the basis of this finding, we investigated asymmetric [3 + 2] cycloadditions, and it was revealed that several kinds of optically active substituted pyrrolidine derivatives containing contiguous stereogenic tertiary and quaternary carbon centers were obtained with high diastereo- and enantioselectivities. In addition, optically active pyrrolidine cores of hepatitis C virus RNA-dependent polymerase inhibitors and potential effective antiviral agents have been synthesized using this [3 + 2] cycloaddition reaction. NMR spectroscopic analysis and observation of nonamplification of enantioselectivity in nonlinear effect experiments suggested that a monomeric calcium species with an anionic ligand was formed as an active catalyst. A stepwise mechanism of the [3 + 2] cycloaddition, consisting of 1,4-addition and successive intramolecular Mannich-type reaction was suggested. Furthermore, modification of the Schiff base structure resulted in a modification of the reaction course from a [3 + 2] cycloaddition to a 1,4-addition, affording 3-substituted glutamic acid derivatives with high diasterero- and enantioselectivities.

Generation of an N-Sodioazomethine Ylide and Its Cycloadditions with α,β-Unsaturated Esters

Treatment of methyl 2-(benzylideneamino)propanoate with sodium hydride in THF generates an N-sodioazomethine ylide, which shows a very poor stereoselectivity in the cycloaddition with methyl acrylate.However, addition of such a base as triethylamine or t-

Cycloaddition vs. Michael Addition in the Metal Halide/Amine-Induced Reactions of α-(Alkylideneamino) Esters with Electron-Deficient Olefins

The lithiated intermediate derived from methyl 2-(benzylideneamino)propanoate and lithium bromide/triethylamine undergoes cycloaddition and Michael addition with methyl acrylate. 1,3-Dipole character of the intermediate is suggested on the basis of the pr

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

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 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

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

5-Endo-Trig Cyclisation and 1,3-Anionic Cycloaddition in Arylimine Derivatives of α-Amino Acid Esters

Michael adducts of imines of α-amino acid esters are converted into a mixture of two stereoisomeric pyrrolidines by benzyltrimethylammonium methoxide (BTAM) apparently by a 5-endo-trig cyclisation.