Synthesis of Enantioenriched γ-Amino-α,β-unsaturated Esters Utilizing Palladium-Catalyzed Rearrangement of Allylic Carbamates for Direct Application to Formal [3 + 2] Cycloaddition

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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.

Original languageEnglish
Pages (from-to)1682-1685
Number of pages4
JournalOrganic letters
Volume19
Issue number7
DOIs
Publication statusPublished - 2017 Apr 7

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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