Organocatalytic enantioselective γ-aminoalkylation of unsaturated ester: access to pipecolic acid derivatives.
The direct γ-carbon functionalization of α,β-unsaturated esters via N-Heterocyclic Carbene (NHC) catalysis is disclosed. This catalytically generated nucleophilic γ-carbon undergoes highly enantioselective additions to hydrazones. The resulting δ-lactam products can be readily transformed to optically enriched pipecolic acid derivatives.
Division of Chemistry & Biological Chemistry, School of Physical & Mathematical Sciences, Nanyang Technological University , Singapore 637371, Singapore.
Jianfeng
J
Xu
Zhichao
Z
Jin
Yonggui Robin
YR
Chi
D000478:Alkylation; D002384:Catalysis; D004952:Esters; D006571:Heterocyclic Compounds / Q000737:chemistry*; D007769:Lactams / Q000138:chemical synthesis* / Q000737:chemistry; D010875:Pipecolic Acids / Q000737:chemistry*; D013237:Stereoisomerism
D004952:Esters; D006571:Heterocyclic Compounds; D007769:Lactams; D010875:Pipecolic Acids; C031345:pipecolic acid