1-Arylfluorenols: Convenient preparation via the ester-mediated nucleophilic aromatic substitution protocol, facile racemization, and intrinsic chiral induction ability

Tetsutaro Hattori, Eiji Koshiishi, Shinya Wada, Nobuyuki Koike, Osamu Yamabe, Sotaro Miyano

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

Novel 1-aryl-9H-fluoren-9-ols 1 were conveniently synthesized by using the ester-mediated nucleophilic aromatic substitution on 2,6- dimethoxybenzoate 2 by aryl Grignard reagents as the key step. Racemic 1- phenylfluorenol 1a was converted to the diastereomeric esters 8 of (S)-2'- methoxy-1,1'-binaphthyl-2-carboxylic acid, which were readily separable by silica-gel column chromatography. Reduction of the optically pure diastereomer (+)-8 with LiAlH4 accompanied an appreciable racemization to give (+)-1a of 89% ee, which provides the first isolation of an optically active fluorenol of defined enantiomeric purity. Intrinsic chiral induction abilities of the 9-fluorenols 1 were examined in the atrolactic acid synthesis from phenylglyoxylates 9 and methylmagnesium iodide with diastereoselectivity of up to 85% de and the binaphthyl coupling of 1- methoxy-2-naphthoates 11 with 2-methoxy-1-naphthylmagnesium bromide with up to 73% de.

Original languageEnglish
Pages (from-to)619-626
Number of pages8
JournalChirality
Volume10
Issue number7
DOIs
Publication statusPublished - 1998 Jan 1

Keywords

  • Asymmetric synthesis
  • Atrolactic acid derivatives
  • Biaryl coupling reaction
  • Diastereoselective reaction
  • Grignard reaction
  • Nucleophilic aromatic substitution
  • Optical resolution

ASJC Scopus subject areas

  • Analytical Chemistry
  • Catalysis
  • Pharmacology
  • Drug Discovery
  • Spectroscopy
  • Organic Chemistry

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