Transition Metal-Catalyzed Cyclopropanation of Alkenes in Water: Catalyst Efficiency and in Situ Generation of the Diazo Reagent
Organic Letters2002Vol. 4(25), pp. 4531–4533
Citations Over TimeTop 10% of 2002 papers
Abstract
[reaction: see text] A cyclopropanation reaction involving ethyl diazoacetate and olefins proceeds with surprisingly high efficiency in aqueous media using Rh(II) carboxylates. Nishiyama's Ru(II) Py-box and Katsuki's Co(II) Salen complexes that allow for highly enantioselective cyclopropanations in organic solvents can also be applied to aqueous cyclopropanations with similar results. In situ generation of ethyl diazoacetate and cyclopropanation also proceeds efficiently. A chemoselective O-H insertion is also possible in water when hydrophobic catalysts and alcohols are used.
Related Papers
- → A Simple Organocatalytic Enantioselective Cyclopropanation of α,β‐Unsaturated Aldehydes(2007)195 cited
- → An enantioselective approach to (−)-platencin via catalytic asymmetric intramolecular cyclopropanation(2010)36 cited
- → Platinum-Catalysed Cyclopropanation of Olefins with Ethyl Diazoacetate(1997)24 cited
- → Some Aspects on the Mechanism of Palladium-complex-catalyzed Decomposition of and Cyclopropanation with Ethyl Diazoacetate(1978)26 cited
- → Cyclopropanation of olefins by ethyl diazoacetate: Copper‐ and copper‐complex‐containing X‐zeolites as the catalysts(1986)19 cited