120109-19-5Relevant academic research and scientific papers
C- and N-Selective Grignard Addition Reactions of α-Aldimino Esters in the Presence or Absence of Zinc(II) Chloride: Synthetic Applications to Optically Active Azacycles
Hatano, Manabu,Yamashita, Kenji,Ishihara, Kazuaki
supporting information, p. 2412 - 2415 (2015/05/27)
Highly practical synthetic methods were developed for the C- and N-selective Grignard addition reactions of N-4-MeOC6H4-protected α-aldimino esters in the presence or absence of zinc(II) chloride. Diastereoselective C-alkyl addition, tandem C-alkyl addition-N-alkylation, and some transformations to synthetically useful optically active azacycles were demonstrated. (Chemical Equation Presented).
STUDIES ON THE REACTION OF α-IMINO ESTERS WITH ORGANOMETALLIC COMPOUNDS
Yamamoto, Yoshinori,Ito, Wataru
, p. 5415 - 5424 (2007/10/02)
Benzylzinc reagent reacted with α-amino ester ( 2 ) at the α-carbon exclusively, though other organometallic reagents such as Mg, Al, Cu, Ti, and B derivatives reacted at the nitrogen atom.Use of the (S)-amine as a chiral auxiliary of 2 created the R chirality at the imino carbon.Very high chiral induction was realized in the reaction of prenylzinc reagent with α-imino 8-(-)phenylmenthyl ester ( 10 ).The reaction of 2 with heteroatom substituted allylic organometallic compounds ( 15 ) gave the corresponding α-heteroatom substituted amino acid derivatives ( 16 ).Here again, the allylic zinc reagent gave the adduct in higher yield than the corresponding Ti, Al, and B reagents.
