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Intermolecular Cyclopropanation versus CH Insertion in RhII-Catalyzed Carbenoid Reactions

✍ Scribed by Paul Müller; Sarah Tohill

Publisher: Elsevier Science
Year: 2000
Tongue: French
Weight: 121 KB
Volume: 56
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(00)00076-4

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✦ Synopsis

The product ratio of intermolecular insertion and cyclopropanation in transition metal-catalyzed diazo decompositions depends strongly upon the metal, its ligands and upon the substituents of the diazo compound. Ethyl diazoacetate (2a) reacts with cyclohexene (1) almost exclusively by cyclopropanation. However, diazomalonate (2d) and methyl 2-diazophenylacetate (2e) in the presence of Rh II catalysts exhibit a marked tendency towards allylic CH insertion. With 1,4-cyclohexadiene (6), methyl 2-diazophenylacetate (2e) in the presence of chiral Rh II catalysts affords the allylic insertion product 7 in almost quantitative yield and with up to 74% ee.

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