Catalytic asymmetric synthesis of 4-nitropyrazolidines: an access to optically active 1,2,3-triamines.

Abstract

The first catalytic enantio- and diastereoselective synthesis of 4-nitropyrazolidines is presented. Asymmetric hydrogen-bonding activation of nitro-olefins facilitated the 1,3-dipolar cycloaddition with hydrazones, affording optically active 4-nitropyrazolidines containing three continuous stereogenic centers as a single diastereomer in up to 99% ee. Furthermore, it is demonstrated that the optically active 4-nitropyrazolidines can be applied as precursors for the synthesis of highly interesting 1,2,3-triamines.