Preparation of Alkenyl Cyclopropanes through a Ruthenium-Catalyzed Tandem Enyne Metathesis−Cyclopropanation Sequence
Journal of the American Chemical Society2005Vol. 128(1), pp. 52–53
Citations Over TimeTop 10% of 2005 papers
Abstract
Acyclic enynes undergo a tandem enyne metathesis/cyclopropanation sequence in the presence of Grubbs' 1st generation metathesis catalyst and diazo compounds. In practice, the acyclic substrates in the presence of the ruthenium alkylidene first undergo a ring-closing enyne metathesis to generate cyclic 1,3-dienes; then upon addition of a diazo compound, these products are cyclopropanated selectively at the more accessible olefin. Overall, the reaction sequence converts acyclic enynes into vinyl cyclopropanes in single operation through two unique ruthenium-catalyzed transformations.
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