Chiral Brønsted Acid Catalysed Kinetic Resolution of Secondary and Tertiary 3-Amido Allylic Alcohols

Jianwen Jin, Lorenzo Carli, Yichao Zhao, Xuehua Zhu, Bo Xia, Philip Wai Hong Chan

Research output: Contribution to journalArticleResearchpeer-review

Abstract

A synthetic method to prepare enantioenriched secondary and tertiary 3-amido allylic alcohols efficiently that relies on their stereoablative enantioselective kinetic resolution (KR) catalysed by a chiral Brønsted acid is described. Achieved at room temperature, the stereoablative asymmetric KR protocol was shown to exhibit excellent functional group tolerance and provided product yields up to 50%, and ee and s values up to 99% and >200. The synthetic utility of the divergent catalytic protocol was exemplified by the 1 mmol scale preparation of one tertiary example and its reduction or bromination to give the corresponding 1,3-amino alcohol and 2-bromo-1,3-amino alcohol derivatives. The suggested asymmetric KR pathways provide rare instances of accomplishing enantioselective discrimination through the dehydration or imine-enamine tautomerisation/retro-aza-aldol reaction of the respective 2° and 3° alcohol substrates.

Original languageEnglish
Pages (from-to)4274-4285
Number of pages12
JournalAdvanced Synthesis and Catalysis
Volume365
Issue number23
DOIs
Publication statusPublished - 5 Dec 2023

Keywords

  • chiral Brønsted acid catalysis
  • enantioselective kinetic resolution
  • stereoablation
  • synthetic methods
  • tertiary alcohols

Cite this