Pd-Catalyzed Acyl C-O Bond Activation for Selective Ring-Opening of α-Methylene-β-lactones with Amines

Christian A. Malapit, Donald R. Caldwell, Nicole Sassu, Samuel Milbin, Amy R. Howell*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

23 Scopus citations

Abstract

A Pd-catalyzed ring-opening of β-lactones with various types of amines (primary, secondary, and aryl) to provide β-hydroxy amides with excellent selectivity toward acyl C-O bond cleavage is reported. The utility of this protocol is demonstrated in an asymmetric kinetic resolution providing enantioenriched α-methylene-β-lactones.

Original languageEnglish (US)
Pages (from-to)1966-1969
Number of pages4
JournalOrganic Letters
Volume19
Issue number8
DOIs
StatePublished - Apr 21 2017
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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