Synthesis of α-Allenic Esters (Acids)

Michel Miesch

doi:10.1055/s-2004-815983

SPECIALTOPIC

Synthesis of α-Allenic Esters (Acids)

Michel Miesch*
Université Louis Pasteur, Faculté de Chimie, Laboratoire de Chimie Organique Synthétique associe au CNRS, 1 rue Blaise Pascal, BP 296/R8, 67008 Strasbourg Cedex, France
Fax: +33(3)90241752; e-Mail: miesch@chimie.u-strasbg.fr;

Abstract

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Abstract

This article focuses on the synthesis of α-allenic esters (or alkane-2,3-dienoates) and their corresponding acids, but does not claim to present all of the synthetic methods of this type of compounds. A brief account dealing with the asymmetric synthesis of α-allenic esters is also presented.

1 Introduction
2 Synthesis of α-Allenic Esters (Acids)
2.1 From Propargyl Derivatives
2.2 From Palladium-Catalyzed Reactions of Propargyl Compounds
2.3 From Horner-Wadsworth-Emmons and Wittig Reactions
2.4 Via Sigmatropic Rearrangements
2.5 From Organometallic Reagents
2.6 From Acetylenic Derivatives
2.7 From β-Keto Esters and ω-Keto Esters
2.8 Via Flash Vacuum Thermolysis (FVT)
2.9 From gem-Difluorocyclopropene
2.10 Miscelleanous
3 Asymmetric Synthesis
4 Conclusion

Key words

alkane-2,3-dienoates - allene carboxylates - acetylenic - propargyl

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