Bis-phosphoric acid derived from BINOL dimer as a chiral brønsted acid catalyst for enantioselective transformations

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Abstract

A chiral bis-phosphoric acid derived from a BINOL (1,1¤-bi-2-naphthol) dimer as a chiral backbone was developed. The catalytic efficiency of this bis-phosphoric acid was compared with that of a reported bis-phosphoric acid having a single BINOL backbone in the Diels-Alder reaction of acrolein with 1,3-dien-1-ylcarbamate. The detailed structural analysis of these bis-phosphoric acid catalysts, coupled with the stereochemical outcome of the Diels-Alder reaction, led to the identification of the specific properties of the bis-phosphoric acid catalysts responsible for the high enantioselectivity.

Original languageEnglish
Pages (from-to)260-263
Number of pages4
JournalChemistry Letters
Volume48
Issue number3
DOIs
Publication statusPublished - 2019 Jan 1

Keywords

  • Asymmetric synthesis
  • Brønsted acid
  • Organocatalysis

ASJC Scopus subject areas

  • Chemistry(all)

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