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3‐(Prop‐2‐enylidene)azetidin‐2‐one Derivatives: Synthesis, structure, and formation of 3‐spiro‐β‐lactams via Diels–Alder reactions
Author(s) -
Ruf Sabine,
Otto HansHartwig
Publication year - 1995
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19950780310
Subject(s) - chemistry , reactivity (psychology) , diels–alder reaction , stereochemistry , organic chemistry , medicinal chemistry , catalysis , medicine , alternative medicine , pathology
Reactions of 3‐silylated β‐lactams ( 1 ) with α,β‐unsaturated ketones give the propylidene‐β‐lactams 3 and the cycloalkenylidene derivatives 5 . Structure and configuration are elucidated by spectroscopic methods, and the reactivity is discussed. While compounds 5 do not react with dienophiles, the ( Z )‐isomers of 3 are the favored substrates for Diels‐Alder reactions yielding the spiro compounds 6 and 7 .