Lewis Acid-catalyzed Decarboxylative Cyanation of Cyclic Enol Carbonates ®Access to Multi-substituted ¢-Ketonitriles®

Haruki Yokoyama, Yoichi Dokai, Natsuki Kimaru, Kodai Saito, Tohru Yamada

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

A Lewis acid-catalyzed decarboxylative substitution reaction of cyclic enol carbonates with a cyanation reagent was developed to give ¢-ketonitriles in good yield. It is proposed that the reaction proceeds through an oxyallyl cation intermediate or its equivalent. Interestingly, cyanation selectively took place at the more hindered site of the intermediate to afford a multi-substituted ¢-ketonitrile. This regioselectivity was observed by the cyanation of a wide range of substrates and is discussed in terms of the reaction mechanism.

Original languageEnglish
Pages (from-to)469-472
Number of pages4
JournalChemistry Letters
Volume51
Issue number4
DOIs
Publication statusPublished - 2022 Apr

Keywords

  • Decarboxylation
  • Lewis acid
  • Substitution reaction

ASJC Scopus subject areas

  • Chemistry(all)

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