134306-43-7

Upstream product

• 621-84-1 O-benzyl carbamate 
• 22979-35-7 Methyl phenyldiazoacetate 
• 67-56-1 methanol 
• 5491-18-9 (S)-N-(benzyloxycarbonyl)phenylglycine 
• 15028-40-7 DL-2-phenylglycine methyl ester hydrochloride 
• 219580-34-4 1-benzyloxycarbonylpyrazole 
• 186581-53-3 diazomethane 
• 501-53-1 benzyl chloroformate 
• 538-51-2 benzylidene phenylamine 
• 1360863-29-1 methyl (Z)-2-(benzyloxycarbonylimino)-2-phenylacetate 
• 5491-18-9 2-(benzyloxycarbonylamino)-2-phenylacetic acid 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 555-16-8 4-nitrobenzaldehdye 
• 24461-61-8 phenylglycine methyl ester 

Downstream Products

• 120226-03-1 5-Benzyloxy-3-phenyl-3H-[1,2,4]triazole-1,2,3-tricarboxylic acid 1,2-diisopropyl ester 3-methyl ester 
• 120226-01-9 5-Benzyloxy-5-hydroxy-3-phenyl-[1,2,4]triazolidine-1,2,3-tricarboxylic acid 1,2-diisopropyl ester 3-methyl ester 
• 24461-61-8 phenylglycine methyl ester 
• 1384465-79-5 1-benzyl 2-methyl (+/-)-2-phenylazetidine-1,2-dicarboxylate 

Relevant academic research and scientific papers

Nitrogen-Doped Carbon Enables Heterogeneous Asymmetric Insertion of Carbenoids into Amines Catalyzed by Rhodium Nanoparticles

Development of stable heterogeneous catalyst systems is a crucial subject to achieve sustainable society. Though metal nanoparticles are robust species, the study of asymmetric catalysis by them has been restricted because methods to activate metal nanopa

Direct ortho -Selective C-H Functionalization of Carboxybenzyl-Protected Arylalkylamines via Ir(III)-Catalyzed C-H Activation

A convenient and practical approach to synthesize ortho-alkynylated arylalkylamines through ortho-selective C-H functionalization has been developed using Cbz-amide as the directing group and Ir(III) as the catalyst. Various substrates were well tolerated, affording the corresponding products in moderate to good yields. Moreover, preliminary mechanistic study revealed the role of the amide as the coordination center to cooperate with the Ir(III) complex during C-H activation. Development of this Cbz-amide-promoted CAr-H functionalization offers a practical approach with potential applications in organic synthesis.

Montmorillonite K10 catalyzed highly regioselective azidolysis of epoxides: A short and efficient synthesis of phenylglycine

A series of β‐hydroxyazides were effectively synthesized from the regioselective ring opening of epoxides by sodium azide using montmorillonite K10 as a novel heterogeneous catalyst in aqueous acetonitrile in good to excellent yields. The utility of this method has been demonstrated by achieving a short synthesis of phenylglycine in 33.5% overall yield.

Formation of Non-Natural α,α-Disubstituted Amino Esters via Catalytic Michael Addition

The enolate monoanion of amino esters is explored, and the first catalytic Michael addition of α-amino esters is demonstrated. These studies indicate that the acidity of the αC-H is the primary factor determining reactivity. Thus, polyfluorophenylglycine amino esters yield novel α-amino esters in the presence of a catalytic amount of a guanidine-derived base and Michael acceptors. Reactivity requires an acidic N-H, which is accomplished using common protecting groups such as N-Bz, N-Boc, and N-Cbz. Calculations and labeling experiments provide insight into the governing principles in which a key C-to-N proton transfer occurs, resulting in an expansion of the scope to include a number of natural amino esters. The study culminates with a late-stage functionalization of peptidic γ-secretase inhibitor, DAPT.

N—H Insertion Reactions Catalyzed by a Dirhodium Metal-Organic Cage: A Facile and Recyclable Approach for C—N Bond Formation

A heterogeneous metal-organic cage based on Rh-Rh bonds [Rh4(pbeddb)4(H2O)2(DMAC)2] (MOC-18; pbeddb2? = 3,3'-(1,3-phenylenebis(ethyne-2,1-diyl))dibenzoate) was applied to the N—H insertion

Rh2(OAc)4 and InCl3 co-catalyzed diastereoselective trapping of carbamate ammonium ylides with aldehydes for the synthesis of β-hydroxyl-α-amino acid derivatives

A Rh2(OAc)4 and InCl3 co-catalyzed three component reaction of diazo compounds, carbamates and aldehydes has been developed to synthesize β-hydroxyl-α-amino acid derivatives in good yields with excellent diastereoselectivity. The reaction is proceeded via trapping of active carbamate ammonium ylide intermediates by aromatic aldehydes.

One-step synthesis of racemic α-amino acids from aldehydes, amine components, and gaseous CO2 by the aid of a bismetal reagent

α-Amino acids are essential resources for human life and are highly useful as building blocks for organic synthesis. The core framework of an α-amino acid can be divided into three basic components: an aldehyde, an amine, and carbon dioxide (CO2). We report herein that a one-step synthesis of α-amino acids has been successfully achieved from these three basic and inexpensive chemicals with a single operation, in which the mixture of an aldehyde, a sulfonamide, and gaseous CO2 was heated at 100 °C in the presence of Bu3Sn-SnBu3 and CsF. In this one-pot sequential protocol, two important intermediates (imine and α-amino stannane) are involved and the stannyl anion generated in situ plays a crucial role, particularly for the efficient stannylation of the imine in the presence of proton sources and for promoting retrostannylation of the undesired α-alkoxy stannane owing to its high stability and tolerance of the presence of proton sources. This methodology enabled the synthesis of a wide range of racemic arylglycine derivatives in high yields. Go retro! α-Amino acids are essential resources for human life and are highly useful as building blocks for organic synthesis. The core framework of an α-amino acid is retrosynthesized to an aldehyde, an amine, and carbon dioxide. A one-step synthesis of α-amin Copyright

A novel method for synthesizing N-alkoxycarbonyl aryl α-imino esters and their applications in enantioselective transformations

A new strategy for the synthesis of N-alkoxycarbonyl aryl α-imino esters in the presence of dirhodium tetraacetate [Rh2(OAc) 4] is reported to produce the desired compounds in high yield (up to 96%) under mild reaction conditions. The application of the synthetic method is demonstrated in enantioselective reduction and Friedel-Crafts reaction of indoles to afford the corresponding chiral arylglycines and indole derivatives, respectively, in high yield and excellent ee. Copyright

Diastereoselectively switchable enantioselective trapping of carbamate ammonium ylides with imines

The diastereoselectively switchable enantioselective trapping of protic carbamate ammonium ylides with imines is reported. The intriguing Rh 2(OAc)4 and chiral Bronsted acid cocatalyzed three-component Mannich-type reaction of a diazo compound, a carbamate, and an imine provides rapid and efficient access to both syn- and anti-α- substituted α,β-diamino acid derivatives with a high level control of chemo-, diastereo-, and enantioselectivity.

New facile alkoxycarbonylating agent, alkyl pyrazole-1-carboxylates. The preparation and the utilities

Alkyl pyrazole-1-carboxylates (2), which were readily prepared from alkyl chloroformate or carbazate in good yields, were provided as the new facile alkoxycarbonylating agents toward the Grignard reagents for the synthesis of one carbon higher carboxylic esters. Also amines were alkoxycarbonylated by 2 to produce the corresponding urethanes even in an aqueous medium. Benzyl 3,5-dimethylpyrazole-1-carboxylate (2d) could be utilized for the Cbz-protection of amino acids and esters in good yield without any racemization.