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Intramolecular amidocyclopropanation reactions using diethoxymethyl-functionalised lactams as organozinc carbenoid precursors

Jerome, L; Sheppard, TD; Aliev, AE; Motherwell, WB; (2009) Intramolecular amidocyclopropanation reactions using diethoxymethyl-functionalised lactams as organozinc carbenoid precursors. Tetrahedron Letters , 50 (26) 3709 - 3712. 10.1016/j.tetlet.2009.03.224. Green open access

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Abstract

Intramolecular amidocyclopropanation reactions of diethoxymethyl-lactams containing a pendant alkene were examined using zinc/TMSCI. With a range of 4-6-membered lactams, bicyclic amidocyclopropanes were obtained with very high diastereoselectivity with a preference for the formation of the More hindered endo-cyclopropane. (C) 2009 Elsevier Ltd. All rights reserved.

Type:Article
Title:Intramolecular amidocyclopropanation reactions using diethoxymethyl-functionalised lactams as organozinc carbenoid precursors
Open access status:An open access version is available from UCL Discovery
DOI:10.1016/j.tetlet.2009.03.224
Publisher version:http://dx.doi.org/10.1016/j.tetlet.2009.03.224
Language:English
Keywords:Lactams, Carbenoids, Cyclopropanes, Zinc, Alkenes, DE-MEIJERE REACTION, REDUCTIVE CYCLOPROPANATION, BICYCLIC CYCLOPROPYLAMINES, MEDIATED CYCLOPROPANATION, STEREOSELECTIVE-SYNTHESIS, AMIDE GROUPS, ACID, ALKENES, AMINOCYCLOPROPANES, VINYLDIAZOMETHANES
UCL classification:UCL > School of BEAMS > Faculty of Maths and Physical Sciences > Chemistry

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