Optically Active 5-(Hydroxyalkyl)- and 5-(Aminoalkyl)pyrazolidin-3-ones by Ring-Chain Transformation of α,β-Unsaturated Lactones or Lactams with Hydrazines

Autor:	Jörg Bohrisch, Jürgen Liebscher, Heike Faltz, Michael Pätzel
Rok vydání:	1996
Předmět:	Chemistry Organic Chemistry Imine Hydrazine Enantioselective synthesis General Chemistry Optically active Ring (chemistry) Medicinal chemistry Benzaldehyde Transformation (genetics) chemistry.chemical_compound Nucleophile Physical and Theoretical Chemistry
Zdroj:	Liebigs Annalen. 1996:1581-1585
ISSN:	1099-0690 0947-3440
DOI:	10.1002/jlac.199619961013
Popis:	α,β-Unsaturated lactones or lactams 1 react with hydrazines 2 via Michael-like addition and subsequent ring transformation by nucleophilic attack of the hitherto unchanged hydrazine nitrogen atom at the carbonyl carbon atom. The addition is highly trans-stereoselective, thus affording optically active hydroxylalkyl- or aminoalkylpyrazolidin-3-ones 4 and 6. These pyrazolidin-3-ones are further transformed to tosylated, acetylated or silylated derivatives 9 or react with benzaldehyde to give the azomethine imine 10.
Databáze:	OpenAIRE
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