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

Begis, G; Cladingboel, DE; Jerome, L; Motherwell, WB; Sheppard, TD; (2009) Asymmetric Synthesis of Aminocyclopropanes and N-Cyclopropylamino Alcohols Through Direct Amidocyclopropanation of Alkenes Using Chiral Organozinc Carbenoids. EUR J ORG CHEM (10) 1532 - 1548. 10.1002/ejoc.200801033.

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Abstract

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)

Type:Article
Title:Asymmetric Synthesis of Aminocyclopropanes and N-Cyclopropylamino Alcohols Through Direct Amidocyclopropanation of Alkenes Using Chiral Organozinc Carbenoids
DOI:10.1002/ejoc.200801033
Keywords:Cyclopropanes, Chiral auxiliaries, Alkenes, Carbenoids, Zinc, ALPHA-AMINO-ACIDS, CATALYTIC CYCLOPROPANATION, STEREOSELECTIVE-SYNTHESIS, CARBONYL-COMPOUNDS, ORGANIC-SYNTHESIS, GENERAL-APPROACH, NITRILES, ROUTE, DERIVATIVES, COMPLEXES
UCL classification:UCL > School of BEAMS > Faculty of Maths and Physical Sciences > Chemistry

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