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Gold(I)‐Catalysed Cycloisomerisation of 1,6‐Cyclopropene‐enes
Author(s) -
Miege Frédéric,
Meyer Christophe,
Cossy Janine
Publication year - 2012
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201200566
Subject(s) - cyclopropene , carbenoid , cyclopropanation , intramolecular force , regioselectivity , olefin fiber , ring (chemistry) , chemistry , bicyclic molecule , electrophile , cycloisomerization , medicinal chemistry , stereochemistry , organic chemistry , catalysis , rhodium
Abstract The gold(I)‐catalysed cycloisomerisation of appropriately substituted 1,6‐cyclopropene‐enes proceeds through regioselective electrophilic ring opening of the three‐membered ring to generate an alkenyl gold carbenoid that achieves the intramolecular cyclopropanation of the remote olefin. This strategy allows straightforward, highly efficient and diastereoselective access to a variety of substituted 3‐oxa‐ and 3‐azabicyclo[4.1.0]heptanes, as well as to bicyclo[4.1.0]heptan‐3‐ol derivatives. Since the isopropylidene group in the resulting cycloisomerisation products can be subjected to ozonolysis, 3,3‐dimethylcyclopropenes behave as interesting surrogates for α‐diazoketones.