Diastereomeric process-based chiral resolution of helical quinone derivatives using (−)-menthyl chloroformate

Mohammad Shahabuddin, Md Sharif Hossain, Takao Kimura, Michinori Karikomi

Research output: Contribution to journalArticlepeer-review

6 Citations (Scopus)

Abstract

Diastereomeric resolution of helically distorted polycondensed bisphenols (1,1′-bibenzo[c]phenanthrene-2,2′-diols: HEBPOLs) 2a–b was conducted utilizing (1R)-(−)-menthyl chloroformate as a chiral resolving agent. Subsequent manipulation produced highly optically pure [>99% enantiomeric excess (ee)] quinone derivatives (P) and (M)-1a–b in very good yields. The absolute configuration of each product was confirmed based on circular dichroism (CD) spectra and X-ray crystal structure analysis.

Original languageEnglish
Pages (from-to)4491-4495
Number of pages5
JournalTetrahedron Letters
Volume58
Issue number48
DOIs
Publication statusPublished - Nov 29 2017
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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