86000-14-8

Upstream product

• 50-00-0 formaldehyd 
• 31469-15-5 1-methoxy-2-methyl-1-trimethylsiloxy-1-propene 
• 62-53-3 aniline 
• 201230-82-2 carbon monoxide 
• 80-62-6 methacrylic acid methyl ester 
• 547-63-7 Methyl isobutyrate 
• 16350-99-5 N-benzylformanilide 
• 91-78-1 1,3,5-triphenylhexahydro-1,3,5-triazine 

Downstream Products

• 112565-66-9 3-(N-phenyl-p-toluenesulphonyl-3-amino)-2,2-dimethylpropionic acid 

Relevant academic research and scientific papers

Facile synthesis of β-anilinopropionates from Lewis acid-induced N-methyleneanilines with ketene acetals

A facile synthesis of β-anilinopropionates was achieved from the reaction of N-methyleneanilines derived from 1,3,5-triphenylhexahydro-1,3,5-triazines with ketene acetals in the presence of Lewis acid.

Rapid Construction of Tetralin, Chromane, and Indane Motifs via Cyclative C-H/C-H Coupling: Four-Step Total Synthesis of (±)-Russujaponol F

The development of practical C-H/C-H coupling reactions remains a challenging yet appealing synthetic venture because it circumvents the need to prefunctionalize both coupling partners for the generation of C-C bonds. Herein we report a cyclative C(sp3)-H/C(sp2)-H coupling reaction of free aliphatic acids enabled by a cyclopentane-based mono-N-protected β-amino acid ligand. This reaction uses inexpensive sodium percarbonate (Na2CO3·1.5H2O2) as the sole oxidant and generates water as the only byproduct. A range of biologically important scaffolds, including tetralins, chromanes, and indanes, can be easily prepared by this protocol. Finally, the synthetic application of this methodology is demonstrated by the concise total synthesis of (±)-russujaponol F in a four-step sequence starting from readily available phenylacetic acid and pivalic acid through sequential functionalizations of four C-H bonds.

Synthesis of β2,2-Amino Esters via Rh-Catalysed Regioselective Hydroaminomethylation

The synthesis of β2,2-amino esters was successfully achieved via Rh-catalysed regioselective hydroaminomethylation of methyl methacrylate with secondary amines using the neutral precursor [Rh(acac)(CO)2]. In this process, the presence of molecular sieves revealed crucial in order to access the final amino ester. For the synthesis of products containing aniline derivatives, the use of the cationic precursor [Rh(COD)2]BF4 and MeCgPPh phosphine as ligand was necessary in a mixture of toluene/DCE as solvent. Effects of the steric and electronic properties of the amines were observed during this study. Interestingly, poisoning effect of CO in the hydrogenation of the imine intermediate was observed when benzyl amine was used. (Figure presented.).

Preparation of conformationally restricted β2,2- and β2,2,3-amino esters and derivatives containing an all-carbon quaternary center

β-Amino acids are routinely incorporated into peptidic drugs to increase their stability and to incur conformational biases. However, the synthesis of highly substituted β-amino acids still represents a great challenge. A new approach to their preparation is reported involving a Vilsmeier-Haack reaction with nonaromatic carbon nucleophiles. The highly challenging preparation of contiguous tertiary and all-carbon quaternary centers was successfully used to generate several β2,2,3-amino esters, such as derivatives of homoproline, homoalanine, and homopipecolinic esters.

Design and synthesis of a water-tolerant chiral indium complex: Application to one-pot three-component Mannich-type reactions in water

A novel chiral indium(III) camphorsulfonate complex prepared from indium trichloride, allyltributylstannane and (1S)-(+)-10-camphorsulfonic acid has been developed as a water-tolerant Lewis acid to afford high yields (up to 99%) in one-pot three-component

Bronsted Acid-Catalyzed Mannich-Type Reactions in Aqueous Media

HBF4-catalyzed Mannich-type reaction of silyl enolates with aldimines took place smoothly in aqueous organic solvent to afford β-aminocarbonyl compounds in high yields. The HBF4-catalyzed Mannich-type reaction also proceeded smoothly

Three component synthesis of β-amino carbonyl compounds using indium trichloride-catalyzed one-pot Mannich-type reaction in water

The use of indium trichloride as catalyst in a one-pot Mannich reaction in water gives high yields for the formation of β-aminoketones/esters/acids is described. The catalyst can be recycled when the reaction is complete (Loh T.-P.; Wei L.-L. Tetrahedron Lett. 1998, 39, 323). (C) 2000 Elsevier Science Ltd.

One-pot Mannich-type reaction in water: HBF4 catalyzed condensation of aldehydes, amines, and silyl enolates for the synthesis of β-amino carbonyl compounds

HBF4 catalyzed Mannich-type reactions of aldehydes, amines, and silyl enolates took place smoothly in water in the presence of a surfactant to afford β-amino carbonyl compounds in high yields. Thieme Stuttgart.

Novel one-pot Mannich-type reaction in water: Indium trichloride-catalyzed condensation of aldehydes, amines and silyl enol ethers for the synthesis of β-amino ketones and esters

Novel one-pot Mannich-type reaction between aldehydes, amines and silyl enol ethers is catalyzed by indium trichloride in water to give β-amino ketones and esters in moderate to good yields.

Trifluoromethanesulfonic Acid-Promoted Reaction of Hexahydro-1,3,5-triazines. Introduction of a Secondary Aminomethyl Grouping into Carboxylates at the α-Position through Ketene Silyl Acetals

Introduction of secondary aminomethyl grouping RNHCH2 into carboxylates at the α-position has been achieved by reaction of hexahydro-1,3,5-triazines with ketene silyl acetals in the presence of a catalytic amount of trifluoromethanesulfonic acid.Keywords