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Ring‐Closing of 1,7‐ and 1,8‐Enynes of Propargylic O , O ‐Acetals by Ruthenium‐Catalysed Intramolecular Metathesis
Author(s) -
Lanfranchi Don Antoine,
Bour Christophe,
Boff Bastien,
Hanquet Gilles
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201000305
Subject(s) - moiety , chemistry , alkyne , intramolecular force , ruthenium , metathesis , acetal , ring closing metathesis , ring (chemistry) , ethylene , stereochemistry , medicinal chemistry , catalysis , organic chemistry , polymer , polymerization
Acyclic 1,7‐ and 1,8‐enynes with the alkyne moiety directly connected to the asymmetric carbon of an ethyl acetal have been obtained in two steps from the corresponding aldehydes. Ring‐closing metathesis of these enynes delivered the corresponding six‐ and seven‐membered cyclic 1,3‐dienes in moderate‐to‐excellent yields. A competitive ethylene insertion into the alkyne moiety leading to trienes was observed for some substrates depending on their structure and relative configuration.