Synthesis of planar-chiral paracyclophanes via samarium(II)-catalyzed intramolecular pinacol coupling

Tsuyoshi Ueda, Nobuhiro Kanomata, Hajime Machida

Research output: Contribution to journalArticle

58 Citations (Scopus)

Abstract

(Chemical Equation Presented) A series of [n]jparacyclophanediols (n = 8-12) was synthesized by samarium-catalyzed pinacol coupling for their ansa-bridge formation. Enantiomerically pure [n]jparacyclophane esters were derived from the diols in a several steps via chiral resolution (for n = 10) or via crystallization-induced asymmetric transformation (for n = 11) by using amino alcohol auxiliaries and their selective cleavages.

Original languageEnglish
Pages (from-to)2365-2368
Number of pages4
JournalOrganic Letters
Volume7
Issue number12
DOIs
Publication statusPublished - 2005 Jun 9

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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