147666-25-9Relevant academic research and scientific papers
A New Diazoacylating Reagent: Preparation, Structure, and Use of Succinimidyl Diazoacetate
Ouihia, Ali,Rene, Loic,Guilhem, Jean,Pascard, Claudine,Badet, Bernard
, p. 1641 - 1642 (1993)
The easily obtained and very stable title compound 1 can be used for direct diazoacylation of aromatic or aliphatic amines, phenols, thiophenol, and peptides under mild conditions.
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
