39684-40-7Relevant academic research and scientific papers
Efficient synthesis of (Z)- and (E)-methyl 2-(methoxyimino)-2-phenylacetate
Wu, Yong-Jin,Huang, Stella,Ng, Alicia,Gao, Qi,Roy Kimura,Langley, David R.
, p. 2144 - 2147 (2010)
Direct oximation of 2-oxo-2-phenylacetate (3) gave the (Z)-methyl 2-(methoxyimino)-2-phenylacetate (1) in 71% yield, while the E oxime 2 was prepared from 3 in 65% yield via oxime isomerization of 2-(methoxyimino)-2-phenylacetic acid (5). Computational st
Double nucleophilic N-alkylation of α-oxime-esters with Grignard reagents
Mizutani, Yusuke,Tanimoto, Hiroki,Morimoto, Tsumoru,Nishiyama, Yasuhiro,Kakiuchi, Kiyomi
, p. 5903 - 5906,4 (2020/08/20)
Double nucleophilic N-alkylation of α-oxime-esters, affording N,N-dialkyl-α-amino acids is herein described. Grignard reagents accomplished double N-alkylations via umpolung and various N,N-dialkylated α-amino acids were successfully synthesized in 15 min. Both electron-withdrawing sulfonyl groups and electron-donating silyl and methyl groups on oximes were available. Alkylmagnesium species and (E)-configuration of α-oxime-ester were essential to this cascade reaction.
