Dynamic Kinetic Resolution Approach for the Asymmetric Synthesis of Tetrahydrobenzodiazepines Using Transfer Hydrogenation by Chiral Phosphoric Acid

Kosaku Horiguchi, Eri Yamamoto, Kodai Saito, Masahiro Yamanaka, Takahiko Akiyama

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

Asymmetric synthesis of tetrahydrobenzodiazepines was achieved by transfer hydrogenation of dihydrobenzodiazepines with benzothiazoline having a hydrogen-bonding donor substituent by means of a newly synthesized chiral phosphoric acid. This method was applicable to various racemic dihydrobenzodiazepines to give the corresponding products in good yields with excellent diastereoselectivities and enantioselectivities taking advantage of the dynamic kinetic resolution. Furthermore, the effect of bulky substituent at 3,3′-position on the catalyst and hydrogen-bonding donor substituent on benzothiazoline was fully elucidated by the theoretical study.

Original languageEnglish
Pages (from-to)8078-8083
Number of pages6
JournalChemistry - A European Journal
Volume22
Issue number24
DOIs
Publication statusPublished - 2016 Jun 6

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Phosphoric acid
Hydrogenation
Hydrogen bonds
Kinetics
Enantioselectivity
Catalysts
phosphoric acid
benzothiazoline

Keywords

  • dynamic kinetic resolution
  • heterocycles
  • hydrogenation
  • organocatalysis
  • stereoselective synthesis

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Dynamic Kinetic Resolution Approach for the Asymmetric Synthesis of Tetrahydrobenzodiazepines Using Transfer Hydrogenation by Chiral Phosphoric Acid. / Horiguchi, Kosaku; Yamamoto, Eri; Saito, Kodai; Yamanaka, Masahiro; Akiyama, Takahiko.

In: Chemistry - A European Journal, Vol. 22, No. 24, 06.06.2016, p. 8078-8083.

Research output: Contribution to journalArticle

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