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Synthesis 2002(2): 0265-0273
DOI: 10.1055/s-2002-19811
DOI: 10.1055/s-2002-19811
PAPER
© Georg Thieme Verlag Stuttgart · New York
Enediolates of Carboxylic Acids in Synthesis: Synthesis of γ-Chloro-β-hydroxy Acids
Further Information
Received
19 September 2001
Publication Date:
03 August 2004 (online)
Publication History
Publication Date:
03 August 2004 (online)
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Abstract
Enediolates from carboxylic acids react readily with cyclic α-chloroketones to give the corresponding γ-chloro-β-alkoxycarboxylate intermediates depending on the ring size. Small ring ketones lead to γ-chloro-β-hydroxy acids in a highly stereoselective way, whereas medium ring ketones give a mixture of β,γ-epoxy acids and γ-lactones.
Key words
neighbouring-group effects - diastereoselectivity - carboxylic acids - carbanions - lactones
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