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Synfacts 2008(9): 0966-0966
DOI: 10.1055/s-2008-1078645
DOI: 10.1055/s-2008-1078645
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag
Stuttgart ˙ New York
Diastereoselective Cyclopropanation of Alkenes with α-Alkyl-α-diazoesters
P. Panne, A. DeAngelis, J. M. Fox*
University of Delaware, Newark, USA
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
22. August 2008 (online)
Significance
Rhodium carbenoids of alkyl-diazoacetates 1 are not generally used in intermolecular reactions because the easily lead to elimination products 4. This is why most successful Rh-catalyzed reactions of diazoacetates use electronically biased push-pull systems (see Review below). The authors have found that rhodium catalysts bearing sterically hindered acetate ligands such as triphenylacetates are competent catalysts for the intermolecular cyclopropanation of various alkenes. In most cases, the reaction was completely diastereoselective.