Synthesis 2004(5): 746-752  
DOI: 10.1055/s-2004-815983
SPECIALTOPIC
© Georg Thieme Verlag Stuttgart · New York

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;
Further Information

Publication History

Received 1 January 2004
Publication Date:
24 February 2004 (online)

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