Enantioselective Copper-Catalyzed Borylative Amidation of Allenes

Seunghwan Byun, Abdikani Omar Farah, Henry R. Wise, Andrew Katchmar, Paul H.Y. Cheong*, Karl A. Scheidt*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

11 Scopus citations

Abstract

An approach for the copper-catalyzed synthesis of enantioenriched amides bearing an α-stereogenic center is disclosed. This method involves the addition of an allyl copper species to an isocyanate and allows access to α-substituted chiral amides in high yields and high-to-excellent enantioselectivities. The utility of α-vinyl β-boryl amides in synthesis is highlighted by the diversification of products to afford highly useful scaffolds. DFT calculations reveal that the catalyst preferentially coordinates to the oxygen of the isocyanate. Enantiocontrol arises from the steric repulsion between the boryl group and the stereodirecting phenyl of the chiral ligand.

Original languageEnglish (US)
Pages (from-to)22850-22857
Number of pages8
JournalJournal of the American Chemical Society
Volume144
Issue number50
DOIs
StatePublished - Dec 21 2022

ASJC Scopus subject areas

  • General Chemistry
  • Biochemistry
  • Catalysis
  • Colloid and Surface Chemistry

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