A highly stereoselective aza-Henry reaction of α-aryl nitromethanes with aromatic N-Boc imines was established by using C1 -symmetric chiral ammonium betaine as a bifunctional organic base catalyst. Various substituted aryl groups for both imines and nitromethanes were tolerated in the reaction, and a series of precursors for the synthesis of unsymmetrical anti-1,2-diaryl ethylenediamines was provided.
Vinylogous nitronate was successfully generated from β,β‐disubstituted nitroolefins for achieving a highly regio‐, diastereo‐, and enantioselective aza Henry reaction under the influence of chiral ammonium betaine of type 1 as an organic‐base catalyst. The present approach greatly expands the synthetic utility of nitroolefins in the development of carbon–carbon bond‐forming reactions (see scheme).
The vinylogous reactivity of α,β-disubstituted nitroolefins was uncovered through the facile generation of the corresponding α-substituted vinylogous nitronates and their use in the development of a highly diastereo- and enantioselective aza-Henry reaction with N-Boc aldimines under the catalysis of chiral ammonium betaines. The novel vinylogous nitronates undergo stereoselective bond formation at the sterically encumbered α-position exclusively, allowing the construction of contiguous tertiary-quaternary stereogenic carbon centers.
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