Jerome, L and Sheppard, TD and Aliev, AE and 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.
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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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