Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2012, Issue 24, Pages 4441-4451Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201200212
Keywords
Asymmetric synthesis; Synthetic methods; C-C coupling; Cobalt; Iron; Nickel; Ruthenium; Hydrovinylation; Alkenes; Regioselectivity
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The intermolecular carboncarbon bond formation between two alkenes also known as 1,2-hydrovinylation reaction can be realised with different transition metal catalysts. The application of styrene derivatives, norbornenes and other alkenes in asymmetric catalysis with a variety of chiral ligands leads to a-chiral alkene products in an atom-economic transformation. Accordingly, the 1,2-hydrovinylation is one of just a few asymmetric transformations which produce stereogenic centres in the absence of polarised functional groups. The 1,4-hydrovinylation of terminal alkenes and 1,3-dienes can be controlled by the electronic nature of the alkene starting material for the selective formation of linear or branched 1,4-dienes. These adducts can be used for the synthesis of 1,3- as well as 1,4-dicarbonyl derivatives upon ozonolysis of suitable intermediates. As an extension of the 1,4-hydrovinylation reaction a cobalt-catalysed 1,4-hydrobutadienylation reaction is reported where two different 1,3-dienes react selectively for the formation of 1,3,6-trienes.
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