title: Synthesis of Enantioenriched γ-Amino-α,β-unsaturated Esters Utilizing Palladium-Catalyzed Rearrangement of Allylic Carbamates for Direct Application to Formal [3 + 2] Cycloaddition.
abstract: An efficient synthesis of enantioenriched γ-amino-α,β-unsaturated esters was developed by utilizing the palladium-catalyzed decarboxylative rearrangement of enantioenriched allylic carbamates possessing an ester moiety at the allylic position. The reaction proceeded in good yield with a high degree of chirality transfer by making use of Xantphos as a superior ligand for the catalyst. The products directly participated in the formal [3 + 2] cycloaddition reaction with tosyl isocyanate under Brønsted base catalysis to afford enantioenriched β,γ-diamino acid derived imidazolidin-2-ones as versatile chiral building blocks.
authors.affiliation: Research and Analytical Center for Giant Molecules, Graduate School of Science and ‡Department of Chemistry, Graduate School of Science, Tohoku University , Aoba-ku, Sendai 980-8578, Japan.
authors.forename: Azusa
authors.identifier: 0000-0001-7227-8579
authors.initials: A
authors.lastname: Kondoh
authors.affiliation: Research and Analytical Center for Giant Molecules, Graduate School of Science and ‡Department of Chemistry, Graduate School of Science, Tohoku University , Aoba-ku, Sendai 980-8578, Japan.
authors.forename: Yuji
authors.initials: Y
authors.lastname: Kamata
authors.affiliation: Research and Analytical Center for Giant Molecules, Graduate School of Science and ‡Department of Chemistry, Graduate School of Science, Tohoku University , Aoba-ku, Sendai 980-8578, Japan.
authors.forename: Masahiro
authors.identifier: 0000-0002-0554-8652
authors.initials: M
authors.lastname: Terada