226900-30-7

Upstream product

• 81477-94-3 N-(diphenylmethylene)glycine tert-butyl ester 
• 100-39-0 benzyl bromide 
• 1013-88-3 Benzophenone imine 
• 75898-47-4 phenylalanine tert-butyl ester hydrochloride 
• 100-44-7 benzyl chloride 
• 100-51-6 benzyl alcohol 

Downstream Products

• 15100-75-1 L-phenylalanine tert-butyl ester hydrochloride 
• 3403-25-6 tert-butyl (2R)-2-amino-3-phenyl-propanoate hydrochloride 
• 16874-17-2 L-phenylalanine tert-butyl ester 
• 3081-28-5 D-phenylalanine tert-butyl ester 
• 27172-85-6 phenylalanine methyl ester hydrochloride 

Relevant academic research and scientific papers

Synthesis and competency of a novel dicationic phase-transfer catalyst

Synthesis and characterization of a novel phase-transfer catalyst, 6,6′ di(triethylammoniummethyl)-2,2′-dihexyloxybi-1,1′- naphthalene, are reported. Preliminary catalytic studies on the alkylation of a glycine derivative show the catalyst to be an effect

Enantioselective alkylation using a new C3 symmetric amine-based chiral phase-transfer catalyst

A new C3 symmetric amine-based chiral phase-transfer catalyst was synthesized. Application of the chiral PTC (1 mol%) in the alkylation of a tert-butyl glycinate-benzophenone Schiff base under mild reaction conditions provided an alkylated prod

Stereoselective deconjugation of macrocyclic α,β-unsaturated esters by sequential amidation and olefin transposition: Application to enantioselective phase-transfer catalysis

The stereoselective synthesis of chiral macrocycles bearing two aliphatic amide functional groups is reported. After the amidation mediated by TBD, a guanidine derivative, the olefin transposition step is performed with a slight excess of t-BuOK. The products are afforded in moderate to good combined yields (up to 59%) and with an excellent syn diastereoselectivity (dr > 49:1). Introducing enantiopure α-branched substituents was possible and it resulted in mixtures of diastereomers, which could be tested as phase-transfer catalysts using the formation of a phenylalanine analog as a test reaction (up to 43% ee). A clear matched-mismatched situation was observed in the two diastereomeric series.

Directing the Cation Recognition Ability of Calix[4]arenes toward Asymmetric Phase-Transfer Catalysis

The recognition abilities of chiral calixarene hosts toward alkali cation guests have been exploited for the first time in asymmetric phase-transfer catalysis. The binding affinities of a series of chiral α-methylbenzylamine-derived calix[4]arene-amides toward Na+ guest have been determined by 1H NMR spectroscopic titration experiments. The good apparent association constant values are consistent with the macrocycles' catalytic efficiency in the asymmetric alkylation reaction of N-(diphenylmethylene)glycine esters under phase-transfer conditions.

N-Heterocyclic olefins as efficient phase-transfer catalysts for base-promoted alkylation reactions

N-Heterocyclic olefins (NHOs) have very recently emerged as efficient promoters for several chemical reactions due to their strong Br?nsted/Lewis basicities. Here we report the novel application of NHOs as efficient phase-transfer organocatalysts for synt

Phase-Transfer Catalysis via a Proton Sponge: A Bifunctional Role for Biscyclopropenimine

The use of a bis(diisopropylamino)cyclopropenimine-substituted bis-protonated proton sponge as a bifunctional phase-transfer catalyst is reported. Experimental studies and DFT calculations suggest it operates simultaneously as a hydrogen bond donor and a

Rate Acceleration of Solid-Liquid Phase-Transfer Catalysis by Rotor-Stator Homogenizer

A rotor-stator homogenizer was found to be an effective mixing tool that accelerated solid-liquid phase-transfer reactions. In the asymmetric alkylation under phase-transfer conditions using the homogenizer, a considerably high turnover frequency was observed. (Figure presented.).

Inhibition of radical reactions for an improved potassium tert-butoxide-promoted 11C-methylation strategy for the synthesis of α-11C-methyl amino acids

α-11C-Methyl amino acids are useful tools for biological imaging studies. However, a robust procedure for the labeling of amino acids has not yet been established. In this study, the 11C-methylation of Schiff-base-activated α-amino a

A Simple Chiral Cu(II) Complex as an Effective Phase-Transfer Catalyst for the Enantioselective Alkylation of Dissymmetric Glycinate Ketimines

Catalytic asymmetric benzylation of a dissymmetric tert-butylglycinate ketimine, incorporating 1-naphthyl and phenyl groups as the Schiff base substituents, under phase-transfer conditions was investigated. It was interesting to note that the sense of asymmetric induction of the alkylation of Z-imine stereoisomer is opposite to that of the corresponding E stereoisomer with a similar degree of enantioselectivity. More interestingly, the chiral Cu(II) complex of the Schiff base derived from (R)-2-phenylglycinol and 2-hydroxy-1-naphthaldehyde was found to catalyze the same reaction under solid-liquid conditions with comparable enantioselectivity (up to 60% ee) with respect to known cinchona alkaloid catalysts. The solvent/base-system parameter was shown to control the optimal catalytic activity. Chirality 27:944-950, 2015.

Phase-transfer and other types of catalysis with cyclopropenium ions

Abstract This work establishes the cyclopropenium ion as a viable platform for efficient phase-transfer catalysis of a diverse range of organic transformations. The amenability of these catalysts to large-scale synthesis and structural modification is demonstrated. Evaluation of the molecular structure of an optimal catalyst reveals some unique structural features of these systems. Finally, a discussion of electronic charge distribution underscores an important consideration for catalyst design. Aromatic ions: Tris(dialkylamino)cyclopropenium ions are shown to be effective carbocationic phase-transfer catalysts for a variety of mainstay transformations. The cyclopropenium platform is shown to be modular and accessible on scale. An X-ray structure and electron-density map revealed some unique features of this architecture (see scheme).