Chiral phosphoric-acid-catalyzed transfer hydrogenation of ethyl ketimine derivatives by using benzothiazoline

Kodai Saito, Kosaku Horiguchi, Yukihiro Shibata, Masahiro Yamanaka, Takahiko Akiyama

Research output: Contribution to journalArticle

25 Citations (Scopus)

Abstract

Chiral phosphoric acid catalyzed transfer hydrogenation of ketimines derived from propiophenone derivatives and reductive amination of alkyl ethyl ketone derivatives were extensively examined in the presence of two representative hydrogen donors. The excellent enantioselective transfer hydrogenation was achieved by use of benzothiazoline as a hydrogen donor. The theoretical studies elucidated that the unsymmetrical structure of benzothiazoline plays an important role in high enantioselective hydrogenation. Asymmetric transfer hydrogenation of aromatic and aliphatic ketimines derived from ethyl ketone derivatives was examined by the combined use of a chiral phosphoric-acid catalyst and a hydrogen donor. The hydrogen donor had a remarkable effect on the enantioselectivity: excellent enantioselectivity was achieved when benzothiazoline was used as the hydrogen donor (see scheme, TRIP=3,3'-bis(2,4,6-triisopropylphenyl)-1,1'-binaphthyl-2,2'- diylhydrogenphosphate).

Original languageEnglish
Pages (from-to)7616-7620
Number of pages5
JournalChemistry - A European Journal
Volume20
Issue number25
DOIs
Publication statusPublished - 2014 Jun 16
Externally publishedYes

Fingerprint

Phosphoric acid
Hydrogenation
Hydrogen
Derivatives
Enantioselectivity
Ketones
Propiophenones
Amination
ketimine
benzothiazoline
phosphoric acid
Catalysts

Keywords

  • hydrogen donor
  • hydrogenation
  • organocatalysis
  • reductive amination
  • theoretical studies

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Chiral phosphoric-acid-catalyzed transfer hydrogenation of ethyl ketimine derivatives by using benzothiazoline. / Saito, Kodai; Horiguchi, Kosaku; Shibata, Yukihiro; Yamanaka, Masahiro; Akiyama, Takahiko.

In: Chemistry - A European Journal, Vol. 20, No. 25, 16.06.2014, p. 7616-7620.

Research output: Contribution to journalArticle

Saito, Kodai ; Horiguchi, Kosaku ; Shibata, Yukihiro ; Yamanaka, Masahiro ; Akiyama, Takahiko. / Chiral phosphoric-acid-catalyzed transfer hydrogenation of ethyl ketimine derivatives by using benzothiazoline. In: Chemistry - A European Journal. 2014 ; Vol. 20, No. 25. pp. 7616-7620.
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AU - Akiyama, Takahiko

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