Chemoselective Oxidative Esterification and Iodocyclization of Hydroxyalkynyl Aldehydes

Shiv Kumar, Monika Patel, Rakesh K. Saunthwal, Akhilesh K. Verma*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

4 Citations (Scopus)

Abstract

We have described the chemoselective behavior of iodine in the oxidative esterification and electrophilic iodocyclization of hydroxyalkynyl aldehydes that contain a primary alcohol moiety. In the presence of an alcohol, which serves as the nucleophile and solvent, the reaction of the hydroxyalkynyl aldehydes and I2 proceeds through a hemiacetal species to give alkyl 4-(3-hydroxyalkynyl)benzoate esters. In CH2Cl2, these substrates undergo an electrophilic iodocyclization through a cyclic iodonium ion to provide a synthetic route for the formation of the bioactive dihydrofuran/pyran ring system.

Original languageEnglish
Pages (from-to)1893-1902
Number of pages10
JournalAsian Journal of Organic Chemistry
Volume6
Issue number12
DOIs
Publication statusPublished - Dec 2017

Keywords

  • aldehydes
  • chemoselectivity
  • cyclization
  • esterification
  • iodine

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