Amidocarbonylation - An efficient route to amino acid derivatives

Matthias Beller, Markus Eckert

Research output: Contribution to journalReview articlepeer-review

129 Scopus citations

Abstract

Atom efficient, multicomponent reactions that lead to high-value products from inexpensive starting materials are of both economic and ecological interest for industrial organic synthesis. α-Amino acids are amongst the most important compounds in chemistry and biology. As well as their biochemical significance as building blocks of peptides and proteins, α-amino acids are also becoming increasingly interesting as fine chemicals. Possibly one of the key reactions in the preparation of these compounds is transition metal catalyzed amidocarbonylation, where the α-amino acid framework is constructed in a single step from an aldehyde, an amide, and carbon monoxide. This article gives a current overview of transition metal catalyzed amidocarbonylation reactions used in the synthesis of α-amino acids derivatives. A classification and summary of the significant features of this three component reaction is first presented together, with an historical introduction. This section is followed by two sections on cobalt- and palladium-catalyzed amidocarbonylation. A discussion of the mechanism of each of the different amidocarbonylation variants form an introduction. Overviews on further synthetic development of the methodology, such as the domino reaction with an amidocarbonylation step and the expansion of the range of starting materials, form the main topics of both variants. The potential of the method is demonstrated with the help of examples of special synthetic utility (for example, the preparation of arylglycines). Finally, possibilities for future developments in transition metal catalyzed amidocarbonylation reactions are proposed on the basis of the current state of knowledge.

Original languageEnglish
Pages (from-to)1010-1027
Number of pages18
JournalAngewandte Chemie International Edition in English
Volume39
Issue number6
DOIs
StatePublished - 17 Mar 2000
Externally publishedYes

Keywords

  • Amidocarbonylation amino acids
  • Cobalt
  • Homogeneous catalysis
  • Palladium

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