Substituent effects on axial chirality in 1-aryl-3,4-dihydroisoquinolines: controlling the rate of bond rotation

Josep Mas Roselló, Samantha Staniland, Nicholas J. Turner, Jonathan Clayden*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)

3 Citations (Scopus)
254 Downloads (Pure)

Abstract

A series of 1-aryl-3,4-dihydroisoquinolines (DHIQs) were synthesized and their barriers to bond rotation were determined by means of VT-NMR, dynamic HPLC or racemization studies. Although they all presented lower rotational stability than the related 1-arylisoquinolines (such as QUINAP), certain 1-aryl-DHIQ structures had a sufficiently high barrier to bond rotation to show axial chirality. These compounds included 1-(2-triflyl-1-naphthyl)-4,5-dihydroisoquinoline 4h and 1-(2-diphenylphosphanyl-1-naphthyl)-4,5-dihydroisoquinoline 4i. This discovery opens the door to the development of a new group of axially chiral N,P ligands for asymmetric synthesis and also potentially to new strategies for the synthesis of axially chiral 1-arylisoquinolines.

Original languageEnglish
Pages (from-to)5172-5177
Number of pages6
JournalTetrahedron
Volume72
Issue number34
Early online date21 Jan 2016
DOIs
Publication statusPublished - 25 Aug 2016

Bibliographical note

Special issue: Methods for controlling axial chirality

Keywords

  • Atropisomers
  • Axial chirality
  • Biaryls
  • Dihydroisoquinolines
  • QUINAP

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