55895-92-6

Upstream product

• 100-51-6 benzyl alcohol 
• 122-63-4 benzyl proprionate 
• 123325-64-4 benzyl 2-methyl-3-oxobutanoate 
• 17831-01-5 H-Ala-OBzl 
• 17831-01-5 DL-alanine benzyl ester 

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• 18854-19-8 benzyl pyruvate 
• 131746-53-7 benzyl 2-bromo-2-fluoropropionate 
• 143998-33-8 benzyl 2-fluoroprop-2-enoate 
• 1107650-22-5 benzyl 2-iodoacrylate 

Relevant academic research and scientific papers

Ru(ii)-Pheox-catalyzed Si-H insertion reaction: construction of enantioenriched carbon and silicon centers

We established a highly enantioselective Si-H insertion reaction to construct chiral centers at the carbon and silicon atoms, using a Ru(ii)-pheox catalyst. The catalytic asymmetric Si-H insertion reaction of α-methyl-α-diazoesters proceeded smoothly with excellent stereoinduction at both the neighboring carbon and silicon atoms (up to 99% yield and 99% ee).

Rhodium(II)/Chiral Phosphoric Acid-Cocatalyzed Enantioselective O–H Bond Insertion of α-Diazo Esters

A rhodium(II)/chiral phosphoric acid system has been developed for the asymmetric catalytic insertion of α-diazo esters into the O–H bond of carboxylic acids to generate an array of synthetically useful α-hydroxy ester derivatives in good ee (up to 95% ee). Furthermore, the substrate scope could be successfully extended to a range of phenols and alcohols with high yield (up to 92%) and excellent enantioselectivity (up to 97%) under mild reaction conditions. Additionally, a density functional theory (DFT) study was performed to elucidate the reaction mechanism. (Figure presented.).

Trifluoromethylthiolation and Trifluoromethylselenolation of α-Diazo Esters Catalyzed by Copper

α-Diazo esters are smoothly converted into the corresponding trifluoromethyl thio- or selenoethers by reaction with Me4NSCF3or Me4NSeCF3, respectively, in the presence of catalytic amounts of copper thiocyanate. This straightforward method gives high yields under neutral conditions at room temperature and is applicable to a wide range of functionalized molecules, including diverse α-amino acid derivatives. It is well-suited for the late-stage introduction of trifluoromethylthio or -seleno groups into drug-like molecules.

Enantioselective Palladium-Catalyzed C-H Functionalization of Indoles Using an Axially Chiral 2,2′-Bipyridine Ligand

A palladium-catalyzed enantioselective C-H functionalization of indoles was achieved with an axially chiral 2,2′-bipyridine ligand, thus providing the desired indol-3-acetate derivatives with up to 98 % ee. Moreover, the reaction protocol was also effecti

Construction of All-Carbon Quaternary Centers through Cu-Catalyzed Sequential Carbene Migratory Insertion and Nucleophilic Substitution/Michael Addition

A Cu-catalyzed three-component cross-coupling reaction of terminal alkyne, α-diazo ester, and alkyl halide has been developed. This transformation involves sequent migratory insertion of copper-carbene and nucleophilic substitution, in which a C(sp)-C(sp3) bond and a C(sp3)-C(sp3) bond are formed successively on a carbenic center. Michael addition acceptors can also be employed instead of alkyl halides that enable Michael addition to be an alternative way to build C(sp3)-C(sp3) bond. This transformation represents a highly efficient method for the construction of all-carbon quaternary centers.

Asymmetric N-H Insertion of secondary and primary anilines under the catalysis of palladium and chiral guanidine derivatives

Efficient enantioselective N-H insertion reactions of secondary and primary anilines were catalyzed by palladium(0) in combination with chiral guanidine derivatives. A broad range of substituted anilines were tolerated, and the corresponding products were obtained in high yield (up to 99 %) with good enantioselectivity (up to 94 % ee) under mild reaction conditions. The N-H insertion mechanism was examined by the study of kinetic isotope effects, control experiments, HRMS, and spectroscopic analysis. Hidden talents: Chiral guanidine derivatives were developed as useful ligands for the enantioselective insertion of carbenoids into the N-H bonds of secondary and primary anilines in combination with palladium(0), which was not previously known to promote asymmetric N-H insertion (see scheme; dba=dibenzylideneacetone). The N-H insertion mechanism was examined by kinetic isotope studies, control experiments, HRMS, and spectroscopic analysis. Copyright

Enantioselective carbenoid insertion into phenolic O-H bonds with a chiral copper(I) imidazoindolephosphine complex

The enantioselective O-H carbenoid insertion reaction with a new chiral copper(I) imidazoindolephosphine complex has been developed. The chiral copper(I) complex catalyzed the insertion of carbenoids derived from α-diazopropionates into the O-H bonds of various phenol derivatives to give the corresponding α-aryloxypropionates with up to 91% ee.

Enantioselective synthesis of α-alkyl-β-ketoesters: Asymmetric Roskamp reaction catalyzed by an oxazaborolidinium ion

Breaking kamp: A catalytic route toward chiral α-alkyl-β- ketoesters using the title reaction of α-alkyl diazoester with aldehydes has been developed (see scheme). The reaction proceeds with high to excellent enantioselectivities and this methodology was applied to a concise two-step synthesis of the natural pheromone sitophilate. Copyright

Catalytic asymmetric roskamp reaction of α-Alkyl-α-diazoesters with aromatic aldehydes: Highly enantioselective synthesis of α-Alkyl-β-keto esters

The first catalytic enantioselective Roskamp reaction of α-alkyl-α-diazoesters with aromatic aldehydes was realized using a simple chiral N, N′-dioxide-scandium(III) complex. Remarkably, with 0.05 mol % catalyst, the reaction was performed well over a series of substrates, giving the desired products chemoselectively in excellent yields (up to 99%) and enantioselectivities (up to 98% ee) under mild conditions. This protocol provides a promising method for the synthesis of chiral α-alkyl-β- keto esters and 1,3-diols.

Exploring the reaction of iodine with α-diazo esters

In this paper we describe the unprecedented reaction between a-diazo esters 1 and iodine. The reaction, carried out in the presence of aqueous NaHCO 3, afforded the Z-isomer of the corresponding unsaturated-2-iodo ester 8, The configuration of