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α‐Chlor‐nitrone IV: Zur Stereochemie der λ‐Lacton‐Synthese und eine Methode zum Aufbau von α‐Methyliden‐λ‐lactonen aus Olefinen. Über synthetische Methoden, 8. (vorläufige) Mitteilung
Author(s) -
Petrzilka Martin,
Felix Dorothee,
Eschenmoser Albert
Publication year - 1973
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.19730560835
Subject(s) - chemistry , diastereomer , stereospecificity , stereochemistry , nitrone , medicinal chemistry , organic chemistry , catalysis , cycloaddition
The Ag + ‐induced reaction between N‐cyclohexyl‐α‐chloro‐propionaldonitrone and the two diastereomeric 2‐butenes in liquid SO 2 is a stereospecific cis ‐addition. The use of N‐cyclo‐hexyl‐α,β‐dichloro‐propionaldonitrone in this type of reaction provides a preparative route from olefines to α‐methylidene‐butyrolactones.