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Updated: Jun 23, 2026

Modification and Functionalization of the Guanidine Group by Tailor-made Precursors
Published on: April 27, 2017
Enantioselective Henry (nitroaldol) reaction catalyzed by axially chiral guanidines
1Department of Chemistry, Graduate School of Science, Tohoku University, Aoba-ku, Sendai, Japan.
Abstract:
The enantioselective activation of nitroalkanes was attempted on the basis of the complexation between chiral guanidinium and nitronate through two hydrogen bonds. The proposed enantioselective activation was applied to the diastereo- and enantioselective Henry (nitroaldol) reaction of nitroalkanes with aldehydes using axially chiral guanidine bases as the catalyst. Optically active nitroaldol products were obtained in acceptable yields with fairly good enantio- and diastereoselectivities at low temperature.
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