32461-34-0Relevant articles and documents
Asymmetric synthesis of amlnocyclopropanes and N-cyclopropylamino alcohols through direct amidocyclopropanation of alkenes using chiral organozinc carbenoids
Begis, Guillaume,Cladingboel, David E.,Jerome, Laure,Motherwell, William B.,Sheppard, Tom D.
experimental part, p. 1532 - 1548 (2009/09/08)
Chiral N-(diethoxymethyl)oxazolidinones, prepared from the corresponding oxazolidinones by heating in trielhyl orthoformate, can be used as organozinc carbenoid precursors for the direct enantioselective amidocyclopropanation of alkenes. The reaction is successful with a wide range of oxazolidinones and alkenes and proceeds with moderate to excellent yield and stereoselectivity. In most cases the trans/exo amidocyclopropane product, is favoured, although certain cyclic alkenes such as indene favour the formation of the endo cyclopropane. The products can be readily elaborated to produce cyclopropylamino alcohols and amino acids. Wiley-VCH Verlag GmbH & Co. KGaA.