Catalytic asymmetric synthesis of 5-membered alicyclic α-quaternary β-amino acids <i>via</i> [3 + 2]-photocycloaddition of α-substituted acrylates
Yuto Kimura, Daisuke Uraguchi, Takashi Ooi
Abstract
The photocatalytically active salt of a cationic iridium polypyridyl complex and a chiral borate is competent to promote a highly stereoselective [3 + 2]-cycloaddition of cyclopropylurea with α-substituted acrylates. This protocol provides straightforward access to a variety of stereochemically defined 5-membered alicyclic α-quaternary β-amino acids, useful building blocks of β-peptides and peptidomimetics.
Topics & Concepts
Alicyclic compoundCycloadditionCatalysisChemistryStereoselectivityAmino acidStereochemistryOrganic chemistryBiochemistryChemical Synthesis and AnalysisSynthesis and Catalytic ReactionsFluorine in Organic Chemistry