CONTROLLING THE STEREOCHEMISTRY IN 2-OXO-ALDEHYDE-DERIVED UGI ADDUCTS THROUGH THE CINCHONA ALKALOID-PROMOTED ELECTROPHILIC FLUORINATION
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Date
2020-08
Authors
Wang, Yuqing
Wang, Gaigai
Peshkov, Anatoly A.
Yao, Ruwei
Hasan, Muhammad
Zaman, Manzoor
Liu, Chao
Kashtanov, Stepan
Pereshivko, Olga P.
Peshkov, Vsevolod A.
Journal Title
Journal ISSN
Volume Title
Publisher
Beilstein Journal of Organic Chemistry
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.
Description
Keywords
Type of access: Open Access, cinchona alkaloids, electrophilic fluorination, enantioselective synthesis, 2-oxo-aldehydes, Ugi reaction
Citation
Wang, Y., Wang, G., Peshkov, A. A., Yao, R., Hasan, M., Zaman, M., Liu, C., Kashtanov, S., Pereshivko, O. P., & Peshkov, V. A. (2020). Controlling the stereochemistry in 2-oxo-aldehyde-derived Ugi adducts through the cinchona alkaloid-promoted electrophilic fluorination. Beilstein Journal of Organic Chemistry, 16, 1963–1973. https://doi.org/10.3762/bjoc.16.163