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Rhodium‐Catalyzed Cycloisomerization Involving Cyclopropenes: Efficient Stereoselective Synthesis of Medium‐Sized Heterocyclic Scaffolds
Author(s) -
Miege Frédéric,
Meyer Christophe,
Cossy Janine
Publication year - 2011
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201101220
Subject(s) - carbenoid , cycloisomerization , cyclopropanation , intramolecular force , rhodium , stereoselectivity , ring (chemistry) , chemistry , alkene , diazo , combinatorial chemistry , stereochemistry , bicyclic molecule , catalysis , medicinal chemistry , organic chemistry
A happy medium : The title reaction of cyclopropenyl carbinols and carbinylamines gives carbo‐ and heterocycles with a [6.1.0] bicyclic ring fused to an aromatic ring (see scheme, Alloc=allyloxycarbonyl, Boc= tert ‐butyloxycarbonyl). These reactions are the first examples of the formation of medium‐sized rings by the intramolecular cyclopropanation of an alkene with a donor‐substituted rhodium carbenoid, which is not generated from a diazo compound.