A telluride-triggered nucleophilic ring opening of monoactivated cyclopropanes

[reaction: see text] Acylcyclopropanemethanol tosylates undergo rapid ring opening at room temperature by the action of lithium telluride to produce the enolate of a homoallylic ketone. The enolate can be protonated to yield the corresponding ketone or treated with benzaldehyde to give the aldol pro...

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Bibliographic Details
Published in:Organic letters 2004-06, Vol.6 (13), p.2225-2228
Main Authors: Avilov, Dmitry V, Malusare, Mahesh G, Arslancan, Engin, Dittmer, Donald C
Format: Article
Language:English
Online Access:Get full text
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Summary:[reaction: see text] Acylcyclopropanemethanol tosylates undergo rapid ring opening at room temperature by the action of lithium telluride to produce the enolate of a homoallylic ketone. The enolate can be protonated to yield the corresponding ketone or treated with benzaldehyde to give the aldol product with good syn or anti diastereoselectivity depending on the conditions.
ISSN:1523-7060
DOI:10.1021/ol0492804