Organocatalytic enantioselective friedel-crafts reaction of 1-naphthols with isatins and an unexpected spontaneous dehydration process

Deyan Wu, Xuwen Zhang, Yong Xu, Yingfei Xue, Jian Li, Wei Wang, Jin Zhu

Research output: Contribution to journalArticlepeer-review

17 Scopus citations

Abstract

An organocatalytic enantioselective Friedel-Crafts alkylation of 1-naphthols with isatins has been developed. The process is catalyzed by a simple cinchona alkaloid derived thiourea and gives biologically interesting, enantioenriched 3-(naphthalen-2-yl)-3-hydroxy-2-oxindoles in moderate to good yields of 42-83% and with good to high enantioselectivity of up to 94% ee. Furthermore, an unexpected intramolecular dehydration reaction proceeds spontaneously with 4-substituted 1-naphthols to offer structurally different ketone oxindoles.

Original languageEnglish (US)
Pages (from-to)480-486
Number of pages7
JournalAsian Journal of Organic Chemistry
Volume3
Issue number4
DOIs
StatePublished - Apr 2014
Externally publishedYes

Keywords

  • Friedel-Crafts alkylation
  • Isatins
  • Naphthols
  • Organocatalysis
  • Oxindoles

ASJC Scopus subject areas

  • Organic Chemistry

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