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Synthesis 2002(2): 0265-0273
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

Salvador Gila, María Kneetemanb, Margarita Parra*a, Enrique Sotocaa
a Dept. Química Orgánica, Univ. Valencia, Dr. Moliner, 50 46100 Burjassot, Valencia, Spain
Fax: +34(96)3983152; e-Mail: Margarita.Parra@uv.es;
b Dept. Química Orgánica, Fac. Ingeniería Química, Univ. Nacional del Litoral, Santiago del Estero 2829, 3000 Santa Fe, Argentina
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Publikationsverlauf

Received 19 September 2001
Publikationsdatum:
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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