Asymmetric transfer hydrogenation of a new N-tosyltetrahydrocarbazole-1-one ester with the Noyori-Ikariya catalyst

DİLEK Ö., Ertürk E.

Organic Communications, vol.16, no.3, pp.134-141, 2023 (ESCI, Scopus) identifier

  • Publication Type: Article / Article
  • Volume: 16 Issue: 3
  • Publication Date: 2023
  • Doi Number: 10.25135/acg.oc2307.2838
  • Journal Name: Organic Communications
  • Journal Indexes: Emerging Sources Citation Index (ESCI), Scopus, Academic Search Premier
  • Page Numbers: pp.134-141
  • Keywords: Asymmetric transfer hydrogenation, chiral tetrahydrocarbazoles, enantioselective lactone synthesis, Noyori–Ikariya ruthenium catalyst, Ntosyltetrahydrocarbazolone
  • Isparta University of Applied Sciences Affiliated: Yes

Abstract

Enantioselective reduction of a new 1-oxotetrahydrocarbazole compound (ethyl 2-(1-oxo-9-tosyl-2,3,4,9- tetrahydro-1H-carbazol-2-yl)acetate) through asymmetric transfer hydrogenation by using the commercially available Noyori–Ikariya ruthenium catalyst and HCO2H/Et3N or HCO2H/DABCO as the hydrogen source have been investigated. High enantiomeric excesses (up to 96% ee) and moderate to good yields (24–72%) for corresponding alcohol and lactone compounds have been achieved. Structures of all compounds have been characterized by spectroscopic techniques.