Metal complexes-catalyzed hydrolysis, alcoholysis, and hydroalkoxylation

Makoto Tokunaga, Akiyuki Hamasaki, Eiji Yamamoto, Hisashi Itoh

Research output: Contribution to journalArticle

1 Citation (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)738-744
Number of pages7
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume68
Issue number7
DOIs
Publication statusPublished - Jul 1 2010

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Coordination Complexes
Hydrolysis
Palladium
Alkenes
Esters
Alcohols
Ruthenium
Phenol
Amides
Gold
Copper
Derivatives
Catalysts
Molecules
Kinetics
Water
Substrates
vinyl ether

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

Metal complexes-catalyzed hydrolysis, alcoholysis, and hydroalkoxylation. / Tokunaga, Makoto; Hamasaki, Akiyuki; Yamamoto, Eiji; Itoh, Hisashi.

In: Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry, Vol. 68, No. 7, 01.07.2010, p. 738-744.

Research output: Contribution to journalArticle

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