Gold-Catalyzed Amide/Carbamate-Linked N, O-Acetal Formation with Bulky Amides and Alcohols

Kosuke Ohsawa, Shota Ochiai, Junya Kubota, Takayuki Doi

Research output: Contribution to journalArticlepeer-review

Abstract

A gold-catalyzed N,O-acetal formation was established to construct an amide/carbamate-linked N,O-acetal substructure with bulky alcohols. The acyliminium cation species generated from o-alkynylbenzoic acid ester in the presence of a gold catalyst is highly reactive and underwent nucleophilic attack of various bulky alcohols and phenols at room temperature under neutral conditions, leading to the corresponding N,O-acetals in yields of 34-89% with good functional group tolerance.

Original languageEnglish
Pages (from-to)1281-1291
Number of pages11
JournalJournal of Organic Chemistry
Volume86
Issue number1
DOIs
Publication statusPublished - 2021 Jan 1

ASJC Scopus subject areas

  • Organic Chemistry

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