98554-96-2

Upstream product

• 555-48-6 2-amino-N-phenyl-acetamide 
• 4801-39-2 2-amino-N-phenylacetamide hydrochloride 
• 95495-83-3 1-phenyl-5-hydroxy-1,2,3-triazole 
• 27904-92-3 N-glycyl>aniline 
• 14661-69-9 p-toluenesulfonylhydrazone glyoxylic acid chloride 
• 62-53-3 aniline 
• 5326-87-4 N-(phenyl)bromoacetamide 

Downstream Products

• 1073903-16-8 (2R,3S)-1-(t-butoxycarbonyl)-3-(3-methoxyphenyl)-N-phenylaziridine-2-carboxamide 
• 1073903-13-5 (2R,3S)-1-(t-butoxycarbonyl)-3-(2-naphthyl)-N-phenylaziridine-2-carboxamide 
• 1073903-11-3 (2R,3S)-1-(t-butoxycarbonyl)-N-phenyl-3-(3-tolyl)aziridine-2-carboxamide 
• 1073903-19-1 (2R,3S)-1-(t-butoxycarbonyl)-3-(4-fluorophenyl)-N-phenylaziridine-2-carboxamide 
• 1073903-15-7 (2R,3S)-1-(t-butoxycarbonyl)-N-phenyl-3-(4-pivaloyloxyphenyl)aziridine-2-carboxamide 
• 1073903-20-4 (2R,3S)-1-(t-butoxycarbonyl)-3-(3-chlorophenyl)-N-phenylaziridine-2-carboxamide 
• 1073902-99-4 (2R,3S)-1-(t-butoxycarbonyl)-N,3-diphenylaziridine-2-carboxamide 
• 1172133-01-5 (2S,3R)-1-(t-butoxycarbonyl)-N,3-diphenylaziridine-2-carboxamide 

Relevant academic research and scientific papers

NovelN-transfer reagent for converting α-amino acid derivatives to α-diazo compounds

A novel universalN-transfer reagent for direct and effective transformation of α-amino ketones, acetamides, and esters to the corresponding α-diazo products under mild basic conditions has been developed. This one-step synthetic approach not only allows for generation of α-substituted-α-diazo carbonyl compounds from α-amino acid derivatives but also permits preparation of α-diazo dipeptides fromN-terminal dipeptides (32 examples, up to 91%).

N-transfer reagent and method for preparing the same and its application

Provided are a novel N-transfer reagent and a method for preparing the same and its application. The N-transfer reagent is represented by the following Formula (I): The various novel N-transfer reagents of the present invention can be quickly prepared by employing different nitrobenzene precursors. The N-transfer reagents can directly convert a variety of amino compounds into diazo compounds under mild conditions. Particularly, the N-transfer reagents can facilitate the synthesis of the diazo compounds. The application of synthesizing diazo compounds of the present invention can greatly decrease the difficulty in operation, increase the safety during experiments, reduce the cost of production and the environmental pollution, and enhance the industrial value of diazo compounds.

Synthesis of Oxindole Derivatives via Intramolecular C–H Insertion of Diazoamides Using Ru(II)-Pheox Catalyst

This work presented the efficient intramolecular aromatic C–H insertion of diazoacetamide. The 1a–1o diazo compounds (except for 1k) were converted into their corresponding oxindoles via an intramolecular C–H insertion reaction in the presence of a Ru catalyst. The Ru-Pheox catalyst was shown to be highly efficient in this transformation in terms of the regioselectivity, producing the desired products in excellent yield (99%). The efficiency of the Ru catalyst reached 580 (TON) and 156 min?1 (TOF).

Efficient Approaches for the Synthesis of Diverse α-Diazo Amides

Metal-catalysed carbenoid chemistry can be exploited for the synthesis of diverse ranges of small molecules from α-diazo carbonyl compounds. In this paper, three synthetic approaches to α-diazo amides are described, and their scope and limitations are determined. On the basis of these synthetic studies, recommendations are provided to assist the selection of the most appropriate approach for specific classes of product. The availability of practical and efficient syntheses of diverse α-diazo acetamides is expected to facilitate the discovery of many different classes of bioactive small molecules.

Catalytic Asymmetric Epoxidation of Aldehydes with Two VANOL-Derived Chiral Borate Catalysts

A highly diastereo- and enantioselective method for the epoxidation of aldehydes with α-diazoacetamides has been developed with two different borate ester catalysts of VANOL. Both catalytic systems are general for aromatic, aliphatic, and acetylenic aldehydes, giving high yields and inductions for nearly all cases. One borate ester catalyst has two molecules of VANOL and the other only one VANOL. Catalysts generated from BINOL and VAPOL are ineffective catalysts. An application is shown for access to the side-chain of taxol.

Catalytic Asymmetric Synthesis of Alkynyl Aziridines: Both Enantiomers of cis-Aziridines from One Enantiomer of the Catalyst

Alkynyl aziridines can be obtained from the catalytic asymmetric aziridination (AZ reaction) of alkynyl imines with diazo compounds in high yields and high asymmetric inductions mediated by a chiral boroxinate or BOROX catalyst. In contrast to the AZ reaction with aryl- and alkyl-substituted imines, alkynyl imines react to give cis-substituted aziridines with both diazo esters and diazo acetamides. Remarkably, however, the two diazo compounds give different enantiomers of the cis-aziridine from the same enantiomer of the catalyst. Theoretical considerations of the possible transition states for the enantiogenic step reveal that the switch in enantiomers results from a switch from Si-face to Re-face addition to the imine, which in turn is related to a switch from reaction with an E-imine in the former and a Z-isomer of the imine in the latter. The imine did it: The aziridination of alkynyl imines with diazo esters and diazo acetamides gives cis-aziridines with very high enantioselectivities. The absolute configuration of the cis-aziridine is reversed for the two diazo compounds even though the same enantiomer of the catalyst is used. The alkynyl imines can isomerize under the reaction conditions and the enantiomeric switch is proposed to result from the preferential reaction of E-imine with diazo esters and Z-imines with diazo acetamides.

A highly enantioselective Darzens reaction between diazoacetamides and aldehydes catalyzed by a (+)-pinanediol-Ti(OiPr)4 system

A highly efficient enantioselective Darzens reaction of aldehydes with diazoacetamides catalyzed by a (+)-pinanediol-Ti(OiPr)4 system has been developed. The cis-glycidic amides were obtained in high yields and with moderate to excellent enantioselectivity (up to 99%).

Ru(II)-Pheox catalyzed N-H insertion reaction of diazoacetamides: Synthesis of N-substituted α-aminoamides

An efficient protocol for the preparation of α-aminoamides was developed via the Ru(II)-dm-Pheox catalyzed N-H insertion reaction of various diazoacetamides with several amines, including aniline. This catalytic N-H insertion reaction was also applied to the synthesis of 2-(2-methylquinolin-4- ylamino)-N-phenylacetamide, a potential antileishmanial agent.

Controlled diastereo-and enantioselection in a catalytic asymmetric aziridination

Chiral polyborate based Bronsted acids prepared from the VANOL and VAPOL ligands are known to catalyze the reaction of diarylmethyl imines with diazoesters to give cis-aziridines. In the present work, this same catalyst is shown to catalyze the reaction of the same imines with diazoacetamides to give trans-aziridines with the same high asymmetric inductions as seen with cis-aziridines, enabling the development of an unprecedented universal catalytic asymmetric aziridination protocol. The substrate scope is broad and includes imines prepared from both electron-rich and electron-poor aromatic aldehydes and also from 1°, 2°, and 3° aliphatic aldehydes. The face selectivity of the addition to the imine was found to be independent of the diazo compounds. The (S)-VANOL or (S)-VAPOL derived catalyst will cause both diazoesters and diazoacetamides to add to the Si-face of the imine when cis-aziridines are formed and both to add to the Re-face of the imine when trans-aziridines are formed.

Trans-selective asymmetric aziridination of diazoacetamides and N-Boc imines catalyzed by axially chiral dicarboxylic acid

Axially chiral dicarboxylic acid (R)-1d catalyzed reaction of diazoacetamides and N-Boc imines provided a novel organocatalytic means for the formation of enantiomerically enriched N-Boc protected trans aziridines. Copyright