87605-05-8Relevant academic research and scientific papers
A highly enantioselective Darzens reaction between diazoacetamides and aldehydes catalyzed by a (+)-pinanediol-Ti(OiPr)4 system
Liu, Gang,Zhang, Daming,Li, Jian,Xu, Guangyang,Sun, Jiangtao
supporting information, p. 900 - 904 (2013/02/25)
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%).
Controlled diastereo-and enantioselection in a catalytic asymmetric aziridination
Desai, Aman A.,Wulff, William D.
supporting information; experimental part, p. 13100 - 13103 (2010/12/19)
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
Hashimoto, Takuya,Uchiyama, Nanase,Maruoka, Keiji
supporting information; experimental part, p. 14380 - 14381 (2009/02/08)
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
Open chair nitrogen compounds. Part X. Thermolysis of α-diazoacetanilides in methanol: a convenient synthesis of α-methoxyacetanilides from ethyl N-(arylazo)glycinate
Nicholas, Kumudini U. K. Gamage,Vaughan, Keith
, p. 799 - 802 (2007/10/02)
α-Diazoacetanilides (4), which are readily available from teh open-chair triazenes (2), undergo thermolysis in methanol solution to afford the α-methoxyacetanilides (5), an apparently rare type of ether/amide derivative.The methanolic thermolysis is inhib
Open-chain nitrogen compounds. Part IV. Synthesis of 5-hydroxy-1,2,3-triazoles from 1-aryl-3-(ethoxycarbonylmethyl)triazenes: a new route to α-diazo-N-arylacetamides
Baines, Kim M.,Vaughan, Keith,Hooper, Donald R.,Leveck, Lorne F.
, p. 1549 - 1556 (2007/10/02)
A series of triazenes of type ArN=N-NH-CH2CO2Et, N-arylazoglycine ethyl esters, have been prepared by coupling the arene diazonium salt, ArN2+*X-, with ethyl glycinate, NH2CH2CO2Et; an electron-withdrawing substituent, e.g.NO2, CN, CO2R, and Cl, in the ortho or para position of the aryl group is essential for efficient coupling.The p-substituted arylazoglycine ethyl esters cyclize when treated with alcoholic potassium hydroxide to afford the potassium salts of the 1-aryl-5-hydroxy-1,2,3-triazoles, which can be obtained free by acidification of the potassium salt solution with acetic acid.Reaction of the potassium salts with acetic anhydride yields the 1-aryl-5-acetoxy-1,2,3-triazoles.The 5-hydroxytriazoles, when heated in ethanol, rearrange to α-diazoacetanilides, ArNH*COCHN2.The diazoamides can be obtained in low yield directly from the triazenes by prolonged refluxing in ethanol. o-Substituted aryltriazenes do not cyclize under the same conditions but fragment to the arylamine.
