28081-31-4Relevant academic research and scientific papers
Diastereo- And Enantioselective Synthesis of Quaternary α-Amino Acid Precursors by Copper-Catalyzed Propargylation
Zhu, Qiongqiong,Meng, Beibei,Gu, Congzheng,Xu, Ye,Chen, Jie,Lei, Chuanhu,Wu, Xiaoyu
, p. 9985 - 9989 (2019/12/24)
A diastereo- and enantioselective propargylic substitution reaction between propargylic carbonates and α-substituted nitroacetates catalyzed by a Cu-pybox complex is described. This method allows the preparation of a series of non-proteinogenic quaternary α-amino acid precursors featuring two contiguous stereogenic centers and a terminal alkyne moiety in high yields with good to excellent diastereo- and enantioselectivities in most cases. The propargylated adducts were elaborated into a diverse set of quaternary α-amino acid derivatives.
Synthesis of α-Nitro Carbonyls via Nitrations in Flow
Chentsova, Anna,Ushakov, Dmitry B.,Seeberger, Peter H.,Gilmore, Kerry
, p. 9415 - 9421 (2016/10/17)
Reported is a safe, rapid method for the synthesis of α-nitro esters via the trapping of nitronium ions. The two-stage nitration and subsequent deacetylation of readily available 1,3-dicarbonyl compounds was achieved using a biphasic semicontinuous approach. α-Nitro esters and amides were obtained in good overall yields (53-84%). Some of the α-nitro-1,3-dicarbonyl intermediates exhibit enhanced reactivity and undergo an acid-catalyzed Nef-type reaction to α-oxo-carbonyls.
CARBON-CARBON BOND FORMATION BY MEANS OF SUBSTITUTION AND ADDITION REACTIONS INVOLVING THE POLYMER-SUPPORTED CARBANION FROM METHYL NITROACETATE
Fiandanese, V.,Naso, F.,Scilimati, A.
, p. 1187 - 1190 (2007/10/02)
A polymer-supported carbanion has been prepared from methyl nitroacetate and reacted with alkyl halides or activated olefins to give α-nitroesters.
