237753-23-0

Upstream product

• 81477-94-3 N-(diphenylmethylene)glycine tert-butyl ester 
• 459-46-1 4-Fluorobenzyl bromide 

Downstream Products

• 611182-82-2 HO-D-Hpla(TIPS)-D-Phe(4-F)-O-t-Bu 

Relevant academic research and scientific papers

Amide-Based Cinchona Alkaloids as Phase-Transfer Catalysts: Synthesis and Potential Application

Herein we present a library of simple amide derivatives of Cinchona alkaloids in the form of quaternary ammonium salts. The obtained derivatives can be generated very easily and efficiently from inexpensive and commercially available substrates. We tested this class of alkaloids in the alkylation of glycine derivative, carried out under phase-transfer catalyst conditions. The presented hybrid catalysts offer both high reaction yields (up to 97%) and high enantioselectivities of the obtained product (up to 94% ee).

The asymmetric alkylation reaction of glycine derivatives catalyzed by the novel chiral phase transfer catalysts

Herein a new series of chiral phase transfer catalysts derived from the cinchona alkaloids were synthesized and applied in the asymmetric alkylation of glycine derivatives with high yields and moderate to excellent ee values (39.5-99.7%).

9-Amino-(9-deoxy)cinchona alkaloid-derived new chiral phase-transfer catalysts

A new class of 9-amino-(9-deoxy)cinchona alkaloid-derived chiral phase-transfer catalysts bearing amino groups was developed by using known cinchona alkaloids as the starting materials. Due to the transformation of the 9-hydroxyl group into a 9-amino functional group, the catalytic performances were significantly improved in comparison with the corresponding first generation phase-transfer catalysts, and excellent yields (92-99%) and high enantioselectivities (87-96% ee) were achieved in the benchmark asymmetric α-alkylation of glycine Schiff base. Based on the special contribution of the amino group to the high yield and enantioselectivity, the possible catalytic mechanism was conjectured. This journal is

Cyclopeptoids as phase-transfer catalysts for the enantioselective synthesis of α-amino acids

The first application of cyclopeptoids in asymmetric phasetransfer catalysis was examined. A small library of nine alternating N-substituted-glycine and proline hexacyclopeptoids was tested in the enantioselective alkylation of N-(diphenyl-methylene)glyci

Design, synthesis, and application of tartaric acid derived N-spiro quaternary ammonium salts as chiral phase-transfer catalysts

A novel class of tartaric acid-derived N-spiro quaternary ammonium salts was synthesised starting from known TADDOLs. These compounds were found to catalyse the asymmetric α-alkylation of glycine Schiff bases with high enantioselectivities and in good yie

Investigations concerning the syntheses of TADDOL-derived secondary amines and their use to access novel chiral organocatalysts

A structurally carefully diversified library of novel TADDOL-derived chiral secondary amines was synthesized and investigated for their applicability to obtain new organocatalysts like chiral Lewis bases and chiral phase-transfer catalysts. The scope and limitations of the developed syntheses routes to access these catalysts as well their catalytic performance in different benchmark reactions were systematically investigated. The most powerful of the catalysts prepared was found to be highly useful for the phase-transfer catalyzed α-alkylation of glycine Schiff base (high yields and up to 93% ee). Georg Thieme Verlag KG Stuttgart · New York.

Highly efficient polymer supported phase-transfer catalysts containing hydrogen bond inducing functional groups

Merrifield resin supported cinchona ammonium salts bearing 2′-fluorobenzene, 2′-cyanobenzene and 2′-N-oxypyridine groups were prepared and applied to the phase-transfer catalytic alkylation of N-(diphenylmethylene)glycine tert-butyl ester for the enantios

Enantioselective reactions of tert-butyl glycinate-benzophenone Schiff base catalyzed by chiral phase-transfer catalyst in aqueous media without any organic solvent

Chiral phase-transfer catalyzed enantioselective alkylations of tert-butyl glycinate-benzophenone Schiff base were investigated in aqueous media without any organic solvent. Reactions in aqueous media smoothly proceeded to give the desired product in high

L-Menthol as new scaffold for designing chiral phase-transfer catalysts

We herein report, a new class of chiral phase-transfer catalysts derived from l-menthol. The moderately good enantioselectivity exhibited by these catalysts have been explained based on single crystal X-ray data and molecular modelling studies.