Enediolates of Carboxylic Acids in Synthesis: Synthesis of γ-Chloro-β-hydroxy Acids

Salvador Gil; María Kneeteman; Margarita Parra; Enrique Sotoca

doi:10.1055/s-2002-19811

PAPER

Enediolates of Carboxylic Acids in Synthesis: Synthesis of γ-Chloro-β-hydroxy Acids

Salvador Gil^a, María Kneeteman^b, Margarita Parra*^a, Enrique Sotoca^a
^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

Abstract

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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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Referenzen

References

<A NAME="RZ10901SS-1">1</A> Mekelburger HB. Wilcos CS. Formation of Enolates, In Comprehensive Organic Synthesis Trost BM. Fleming I. Pergamon; Oxford: 1991. p.99-131

<A NAME="RZ10901SS-2">2</A> Thomson CM. Dianion Chemistry in Organic Synthesis CRC Press; Boca Raton: 1994. p.88-129

<A NAME="RZ10901SS-3">3</A> Brun EM. Gil S. Mestres R. Parra M. Villar F. Tetrahedron Lett. 1998, 39: 1055

<A NAME="RZ10901SS-4">4</A> Yadav VK. Jeyaraj DA. Balamurugan R. Tetrahedron 2000, 56: 7581

<A NAME="RZ10901SS-5">5</A> Brun EM. Gil S. Mestres R. Parra M. Tetrahedron 1998, 54: 15305

<A NAME="RZ10901SS-6">6</A> Brun EM. Gil S. Parra M. Synthesis 2000, 1160

<A NAME="RZ10901SS-7">7</A> Epstein WW. Sonntag AC. J. Org. Chem. 1967, 32: 3390