Asymmetric Synthesis of Aminocyclopropanes andN-Cyclopropylamino Alcohols Through Direct Amidocyclopropanation of Alkenes Using Chiral Organozinc Carbenoids

Chiral N-(diethoxymethyl)oxazolidinones, prepared from the corresponding oxazolidinones by heating in triethyl orthoformate can he used as organozinc carbenoid precursors for the direct enantioselective amidocyclopropanation of alkenes. The reaction is successful with it wide range of oxazolidinones and alkenes and proceeds with moderate to excellent, yield and stereoselectivity. In most cases the trans/exo amido-cyclopropane product is favoured, although certain cyclic alkenes such is indene favour the formation of the endo cyclopropane. The products can be readily elaborated to produce cyclopropylamino alcohols and amino acids. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)