360074-81-3Relevant academic research and scientific papers
Asymmetric allylation of α-ketoester-derived N-benzoylhydrazones promoted by chiral sulfoxides/N-oxides lewis bases: Highly enantioselective synthesis of quaternary α-substituted α-allyl-α-amino acids
Reyes-Rangel, Gloria,Bandala, Yamir,Garcia-Flores, Fred,Juaristi, Eusebio
, p. 529 - 540 (2013)
Chiral sulfoxides/N-oxides (R)-1 and (R,R)-2 are effective chiral promoters in the enantioselective allylation of α-keto ester N-benzoylhydrazone derivatives 3a, 3b, 3c, 3d, 3e, 3f, 3g to generate the corresponding N-benzoylhydrazine derivatives 4a, 4b, 4c, 4d, 4e, 4f, 4g, with enantiomeric excesses as high as 98%. Representative hydrazine derivatives 4a, 4b were subsequently treated with SmI2, and the resulting amino esters 5a, 5b with LiOH to obtain quaternary α-substituted α-allyl α-amino acids 6a, 6b, whose absolute configuration was assigned as (S), with fundament on chemical correlation and electronic circular dichroism (ECD) data. 2013 Wiley Periodicals, Inc.
Enantioselective Catalytic Allylation of Acyclic Ketiminoesters: Synthesis of α-Fully-Substituted Amino Esters
Bhakta, Urmibhusan,Kattamuri, Padmanabha V.,Siitonen, Juha H.,Alemany, Lawrence B.,Kürti, László
, p. 9208 - 9211 (2019)
We report the first direct catalytic enantioselective allylation of acyclic α-ketiminoesters to afford α-allyl-α-aryl and α-allyl-α-trifluoromethyl amino esters in excellent isolated yield (91-99%) and with high optical purity (90-99+% ee). The allylation
