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

DİLEK Ö., Ertürk E.

Organic Communications, cilt.16, sa.3, ss.134-141, 2023 (ESCI, Scopus) identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 16 Sayı: 3
  • Basım Tarihi: 2023
  • Doi Numarası: 10.25135/acg.oc2307.2838
  • Dergi Adı: Organic Communications
  • Derginin Tarandığı İndeksler: Emerging Sources Citation Index (ESCI), Scopus, Academic Search Premier
  • Sayfa Sayıları: ss.134-141
  • Anahtar Kelimeler: Asymmetric transfer hydrogenation, chiral tetrahydrocarbazoles, enantioselective lactone synthesis, Noyori–Ikariya ruthenium catalyst, Ntosyltetrahydrocarbazolone
  • Isparta Uygulamalı Bilimler Üniversitesi Adresli: Evet

Özet

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.