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

Short Report

JOURNAL 2838

Organic Communications
VOLUME & ISSUE
Available Online: September 14,2023
PAGES
p.1 - 8
DOI ADDRESS
http://doi.org/10.25135/acg.oc2307.2838
(DOI number will be activated after the manuscript has been available in an issue.)
STATISTICS
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AUTHORS
  • Erkan Ertürk
  • Ömer Dİlek
PDF OF ARTICLE

GRAPHICAL ABSTRACT

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.

 KEYWORDS
  • Asymmetric transfer hydrogenation
  • Noyori–Ikariya ruthenium catalyst
  • Chiral tetrahydrocarbazoles
  • N-Tosyltetrahydrocarbazolone
  • Enantioselective lactone synthesis

SUPPORTING INFORMATION

Supporting Information
Download File 156-OC-2307-2838-SI.pdf (910.58 KB)