Aryl λ3-Iodane-Mediated 6-exo-trig Cyclization to Synthesize Highly Substituted Chiral Morpholines

Jaya Kishorevandavasi, Wan Ping Hu, Gopal Chandrusenadi, Hui Ting Chen, Hsing Yin Chen, Kuang Chan Hsieh, Jeh Jeng Wang*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

10 Scopus citations

Abstract

A mild and efficient transition metal-free approach has been developed for the synthesis of highly substituted chiral morpholines from alkenols by amino acid-derived iodine(III) reagents via a 6-exo-trig cyclization. The key features of this work include the formation of three chiral centers with a high diastereomeric ratio, broad functional group compatibility, and atom/time economic methodology.

Original languageEnglish
Pages (from-to)2788-2794
Number of pages7
JournalAdvanced Synthesis and Catalysis
Volume357
Issue number13
DOIs
StatePublished - 1 Sep 2015

Keywords

  • 6-exo-trig cyclization
  • alkenes
  • halo-etherification
  • morpholines
  • λ-iodanes

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