Organocatalyzed Asymmetric Vinylogous Allylic–Allylic Alkylation of Morita–Baylis–Hillman Carbonates with Olefinic Azlactones: Facile Access to Chiral Multifunctional α‑Amino Acid Derivatives

Vinylogous reactivity of olefinic
azlactones was realized through
the development of a chiral amine-catalyzed highly stereoselective
allylic–allylic alkylation with Morita–Baylis–Hillman
carbonates. The Lewis base activation of electrophile and Brønsted
base activation of nucleophile were efficiently combined, giving access
to multifunctional acyclic α-amino acid derivatives in a highly
stereocontrolled manner. The synthetic utility of these versatile
synthons was further demonstrated by the facile synthesis of protected
cyclic quaternary α-amino acids.