Volume 31, Issue 51
Preparative Organic Chemistry
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ChemInform Abstract: Generation of Metalloenamines by Carbon—Carbon Bond Formation: Ring Opening Reactions of 2-Methyleneaziridines with Organometallic Reagents.

Jerome F. Hayes

Jerome F. Hayes

Sch. Chem., Univ. Exeter, Exeter, Devon EX4 4QD, UK

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Michael Shipman

Michael Shipman

Sch. Chem., Univ. Exeter, Exeter, Devon EX4 4QD, UK

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Heather Twin

Heather Twin

Sch. Chem., Univ. Exeter, Exeter, Devon EX4 4QD, UK

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First published: 31 May 2010

Abstract

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ChemInform Abstract

Treatment of 2-methyleneaziridines such as (I) with Grignard reagents in the presence of Cu(I) results in a regioselective ring-opening furnishing metalloenamines of type (III), which immediately react with electrophiles to produce ketones (V) (6 examples).

chemical structure image

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