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Enantioselective Aza-Henry Reaction Catalyzed by a Bifunctional Organocatalyst

Organic Letters · 2004 · Vol. 6(4) · pp. 625–627
Tomotaka OkinoSatoru NakamuraTomihiro FurukawaYoshiji Takemoto

Abstract

[reaction: see text] The aza-Henry reaction of imines with nitroalkanes was promoted by chiral thiourea with an N,N-dimethylamino group to give beta-nitroamines with good enantioselectivity. Various N-protected imines were examined as substrates. N-Phosphinoylimine gave the best result in terms of chemical yield and enantioselectivity (up to 91% yield, up to 76% ee).

Asymmetric Synthesis and CatalysisAsymmetric Hydrogenation and CatalysisChemical Synthesis and AnalysisChemistryEnantioselective synthesisBifunctionalThioureaYield (engineering)CatalysisOrganocatalysisNitroaldol reactionOrganic chemistryReaction conditions
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