Controlling the stereochemistry in 2-oxo-aldehyde-derived Ugi adducts through the cinchona alkaloid-promoted electrophilic fluorination

Yuqing Wang, Gaigai Wang, Anatoly A. Peshkov, Ruwei Yao, Muhammad Hasan, Manzoor Zaman, Chao Liu, Stepan Kashtanov, Olga P. Pereshivko*, Vsevolod A. Peshkov*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

In this report, we introduce a new strategy for controlling the stereochemistry in Ugi adducts. Instead of controlling stereochemistry directly during the Ugi reaction we have attempted to stereodefine the chiral center at the peptidyl position through the post-Ugi functionalization. In order to achieve this, we chose to study 2-oxo-aldehyde-derived Ugi adducts many of which partially or fully exist in the enol form that lacks the aforementioned chiral center. This in turn led to their increased nucleophilicity as compared to the standard Ugi adducts. As such, the stereocenter at the peptidyl position could be installed and stereodefined through the reaction with a suitable electrophile. Towards this end, we were able to deploy an asymmetric cinchona alkaloid-promoted electrophilic fluorination producing enantioenriched post-Ugi adducts fluorinated at the peptidyl position.

Original languageEnglish
Pages (from-to)1963-1973
Number of pages11
JournalBeilstein Journal of Organic Chemistry
Volume16
DOIs
Publication statusPublished - 11 Aug 2020

Keywords

  • 2-oxo-aldehydes
  • Cinchona alkaloids
  • Electrophilic fluorination
  • Enantioselective synthesis
  • Ugi reaction

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