Highly atom efficient catalytic reactions utilizing water and alcohols as reagents

Akiyuki Hamasaki, Eiji Yamamoto, Hisashi Itoh, Makoto Tokunaga

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

In this accounts, we describe our recent studies on hydrolysis, alcoholysis, and addition of alcohols to organic molecules. The reactions utilizing water and alcohols as a reagent are one of the most basic and simple reactions. The palladium-catalyzed asymmetric hydrolysis and alcoholysis of vinyl ethers gave valuable axially chiral 1,1′-bi-2-naphthol and 1,1′-bi-2-phenol derivatives and chiral P-chirogenic compounds in optically active form. The reaction is applied for hydrolytic deallylation of N-allyl amide and allyl esters. The later one was achieved by palladium/ruthenium dual catalysts which is the first example of catalytic irreversible ester hydrolysis. Gold complexes also catalyzed vinyl ether alcoholysis and hydroalkoxylation of olefins. In the later reaction, simple unactivated olefins can be used as substrates and gave the product in 92% yield. The copper-DTBM-SEGPHOS complex catalyzed alcoholysis of azlactones which is the first example showing zero-order kinetic resolution.

Original languageEnglish
Pages (from-to)202-210
Number of pages9
JournalJournal of Organometallic Chemistry
Volume696
Issue number1
DOIs
Publication statusPublished - Jan 1 2011

    Fingerprint

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry
  • Materials Chemistry

Cite this