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Synthesis 2008(8): 1221-1226
DOI: 10.1055/s-2008-1067002
DOI: 10.1055/s-2008-1067002
PAPER
© Georg Thieme Verlag Stuttgart · New York
Development of a Robust and Practical Process for the Darzens Condensation and α,β-Epoxide Rearrangement: Scope and Limitations of the Methodology
Further Information
Publication History
Received
19 December 2007
Publication Date:
27 March 2008 (online)


Abstract
A practical and robust process for the Darzens condensation of substituted benzaldehydes and subsequent α,β-epoxy rearrangement is reported. The process developed is both amenable to large scale and parallel synthesis. While electron-poor benzaldehydes gave mixtures of aryl ketones and 2-substituted aryl ketones in mediocre to low yields, electron-rich benzaldehydes were found to react in high yields with complete regioselectivity to form 2-substituted aryl ketones.
Key words
condensation - rearrangement - regioselectivity - homologation - decarboxylation