Lewis acid catalysis and ligand exchange in the asymmetric binaphthol-catalyzed propargylation of ketones

Matthew N. Grayson, Jonathan M. Goodman

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

1,1′-Bi-2-naphthol (BINOL)-derived catalysts catalyze the asymmetric propargylation of ketones. Density functional theory (DFT) calculations show that the reaction proceeds via a closed six-membered transition structure (TS) in which the chiral catalyst undergoes an exchange process with the original cyclic boronate ligand. This leads to a Lewis acid type activation mode, not a Brønsted acid process, which accurately predicts the stereochemical outcome observed experimentally.

Original languageEnglish
Pages (from-to)8796-8801
Number of pages6
JournalJournal of Organic Chemistry
Volume78
Issue number17
DOIs
Publication statusPublished - 6 Sep 2013

ASJC Scopus subject areas

  • Organic Chemistry

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