Enantioselective Intramolecular Nicholas Reaction Catalyzed by Chiral Phosphoric Acid: Enantioconvergent Synthesis of Seven-Membered Cyclic Ethers from Racemic Diols

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

An enantioconvergent intramolecular Nicholas reaction of racemic diols was developed using BINOL- and SPINOL-derived phosphoric acids as the chiral Brønsted acid catalyst. The developed reaction features an efficient approach to the synthesis of seven-membered cyclic ethers in a highly enantioselective manner. Further derivatization of the enantioenriched cyclic ethers, initiated by the de-complexation of the dicobalt species, afforded densely functionalized cyclic ethers having an unsaturated diester moiety without loss of enantiomeric excess.

Original languageEnglish
Pages (from-to)13917-13921
Number of pages5
JournalAngewandte Chemie - International Edition
Volume57
Issue number42
DOIs
Publication statusPublished - 2018 Oct 15

Keywords

  • Brønsted acids
  • asymmetric catalysis
  • cyclizations
  • ethers
  • organocatalysis

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Fingerprint Dive into the research topics of 'Enantioselective Intramolecular Nicholas Reaction Catalyzed by Chiral Phosphoric Acid: Enantioconvergent Synthesis of Seven-Membered Cyclic Ethers from Racemic Diols'. Together they form a unique fingerprint.

  • Cite this