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Observations on the direct amidocyclopropanation of alkenes using organozinc carbenoids

Motherwell, WB; Begis, G; Cladingboel, DE; Jerome, L; Sheppard, TD; (2007) Observations on the direct amidocyclopropanation of alkenes using organozinc carbenoids. Tetrahedron , 63 (28) 6462 - 6476. 10.1016/j.tet.2007.03.027. Green open access

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Abstract

A series of amidocyclopropanes were prepared by direct amidocyclopropanation of alkenes, using organozinc carbenoids generated from readily available diethoxymethylamides. The amidocyclopropanation of monosubstituted alkenes led to selective formation of the trans-amidocyclopropane in most cases, but with more substituted alkenes, the stereochemical outcome of the cyclopropanation reactions was unpredictable. The amidocyclopropane products can be readily elaborated to structurally interesting cyclopropane containing amino acids or amino alcohols.

Type: Article
Title: Observations on the direct amidocyclopropanation of alkenes using organozinc carbenoids
Location: Berlin, GERMANY
Open access status: An open access version is available from UCL Discovery
DOI: 10.1016/j.tet.2007.03.027
Publisher version: http://dx.doi.org/10.1016/j.tet.2007.03.027
Language: English
Additional information: 8th Tetrahedron Symposium on Challenges in Organic Chemistry, Berlin, GERMANY, JUN 27-29, 2007
Keywords: CARBONYL-COMPOUNDS, AMINO-ACIDS, CYCLOPROPANATION, COMPLEXES, GENERATION, OLEFINS, DERIVATIVES, DIETHOXYMETHYL, ISOMERIZATION, AMIDES
UCL classification: UCL > Provost and Vice Provost Offices
UCL > Provost and Vice Provost Offices > UCL BEAMS
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences > Dept of Chemistry
URI: http://discovery.ucl.ac.uk/id/eprint/170130
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