164471-45-8Relevant academic research and scientific papers
1,2-Asymmetric Induction in the Zwitterionic Claisen Rearrangement of Allylamines
Nubbemeyer, Udo
, p. 3773 - 3780 (1995)
A zwitterionic Claisen rearrangement has been developed for optically active N-allylpyrrolidines using a two-phase system.The inherent-1,2 asymmetric induction was investigated for the generation of a new C-C bond adjacent to a chiral C-O function.The reaction with acetyl chloride led to a small diastereomeric excess, whereas the rearrangement with propionyl chloride proceeded with a high simple and a high induced diastereoselection.The resulting γ,δ-unsaturated amides were cyclized to the corresponding optically active γ-butyrolactones, which are useful intermediates in natural product synthesis.
