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Diels–Alder Reactions for the Construction of Cyclopropylarenes
Author(s) -
Arndt Marion,
Hilt Gerhard,
Khlebnikov Alexander F.,
Kozhushkov Sergei I.,
de Meijere Armin
Publication year - 2012
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.201200105
Subject(s) - chemistry , cycloaddition , regioselectivity , moiety , steric effects , diels–alder reaction , cobalt , ligand (biochemistry) , ring (chemistry) , medicinal chemistry , catalysis , organic chemistry , biochemistry , receptor
The straightforward synthesis of new bicyclopropyl‐substituted alkynes and 1,3‐dienes and their application in cobalt‐catalyzed Diels–Alder reactions are described. The cycloaddition processes generated the desired bicyclopropyl‐substituted arene derivatives in moderate to good yields, depending on the steric congestion of the reaction partners. The regioselectivity of the cycloaddition was controlled by the ligand coordinated to the cobalt center. The cyclopropyl moiety remained unchanged over the course of the Diels–Alder reaction, indicating that no radical type intermediates were formed. Only in a single case did the DDQ oxidation of the primarily formed dihydroaromatic product lead to ring opening of a cyclopropyl subunit. In all of the other cases, cyclopropyl‐modified arenes with various functionalities were obtained.