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Asymmetric Cα‐Alkylation of Pipecolic Acid via Curtin‐Hammett Controlled Diastereoselective N‐Alkylation
Author(s) -
Cho Hyunkyung,
Jung Jaehyun,
Kim Jinju,
Park Soojun,
Kim Sanghee
Publication year - 2019
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201900220
Subject(s) - chemistry , pipecolic acid , alkylation , yield (engineering) , bicyclic molecule , selectivity , stereochemistry , organic chemistry , catalysis , amino acid , biochemistry , materials science , metallurgy
An efficient asymmetric synthetic approach for the synthesis of Cα‐substituted pipecolic acid has been investigated through utilizing an N‐fused bicyclic system. Despite the fluxionality of the pipecolic imidazolidinone, N‐alkylation proceeded in high yield with excellent selectivity. The subsequent [2,3]‐Stevens rearrangement afforded Cα‐substituted pipecolic acid derivatives successfully. The computational study revealed that the diastereoselectivity during N‐alkylation is governed by Curtin‐Hammett kinetics.