Assembly of 4-Substituted 3-Nitro-1,2,3,4-tetrahydropyridines via Organocatalytic Michael Addition

An organocatalytic Michael addition of protected 2‐amino‐1‐nitroethanes to α,β‐unsaturated aldehydes followed by treatment with TFA afforded 4‐substituted 3‐nitro‐1,2,3,4‐tetrahydropyridines with good diastereoselectivity and excellent enantioselectivity. Good yields were observed in the case of β‐a...

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Veröffentlicht in:Advanced synthesis & catalysis 2012-04, Vol.354 (6), p.991-994
Hauptverfasser: Huo, Lele, Ma, Anqi, Zhang, Yihua, Ma, Dawei
Format: Artikel
Sprache:eng
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Zusammenfassung:An organocatalytic Michael addition of protected 2‐amino‐1‐nitroethanes to α,β‐unsaturated aldehydes followed by treatment with TFA afforded 4‐substituted 3‐nitro‐1,2,3,4‐tetrahydropyridines with good diastereoselectivity and excellent enantioselectivity. Good yields were observed in the case of β‐aryl‐substituted α,β‐unsaturated aldehydes as the substrates, while moderate yields were obtained when β‐alkyl‐substituted α,β‐unsaturated aldehydes were used.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201100903