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20.5.3 Product Subclass 3: Butenedioic and Butynedioic Acid Esters

DOI: 10.1055/sos-SD-020-00864

Masse, C. E.Science of Synthesis, (200720957.

General Introduction

The butenedioic and butynedioic acid and ester subclasses represent a versatile group of building blocks in organic synthesis. They are frequently utilized in a multitude of organic transformations including DielsAlder reactions,[‌1‌] conjugate additions,[‌2‌] and hydrogenations. The synthesis of these substrates often makes use of naturally occurring reagents such as amino acids, tartaric acid, or malic acid derivatives. As a note regarding nomenclature, the (E)-but-2-enedioate isomer is commonly referred to as the fumarate derivative while the corresponding Z-isomers are referred to as maleate derivatives. The reader will note that the preparation of butynedioate esters has been omitted from this review. Their omission stems from the fact that most reports for the preparation involve a simple esterification of the corresponding butynedioic acids, whose preparations are covered in Section 20.2.3. The following sections will attempt to detail some of the more commonly exploited methods for the synthesis of butenedioic acid esters. Relevant examples will be outlined in a tabular format and experimental procedures as well as critical characterization data will be provided whenever possible.

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