Stereoselective Synthesis

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Schematic representation of a stereoselective synthesis: The structure on the right is preferably - or exclusively - created.

As Stereoselective synthesis is in the chemical , a method referred to which a molecule targeted is built up with a fixed three-dimensional structure, so that one of several possible stereoisomers of a is preferably formed.

target

In addition to the general objective of chemical synthesis , bonds to make controlled occur in this case one or more new stereogenic centers . The goal of a stereoselective synthesis is now the selective, i.e. predominant, production of a certain stereoisomer . In a stereospecific synthesis , only one pure stereoisomer is formed.

Stereoselective syntheses can take place if at least one of the substances involved in the reaction has a clear structure ( configuration ). On the one hand, natural substances from the chiral pool are used as starting materials or auxiliaries; on the other hand, these or artificially produced substances can be used in a catalytic reaction. A special case of stereoselective catalysis (also called chiral or asymmetric catalysis with restrictions ) is the use of enzymes . The stereoselective synthesis is particularly important in the production of biologically active substances and drugs, since the spatial structure in natural processes is often decisive for the pharmacological or general biological effect and the effect of a substance.

Both in industry and in science, the development of new stereoselective syntheses is therefore one of the most intensively researched areas of modern chemistry, especially organic chemistry.

Individual evidence

  1. ↑ Bernhard Testa: Fundamentals of Organic Stereochemistry , Verlag Chemie, Weinheim, 1983, pp. 147-162, ISBN 3-527-25935-X .
  2. ↑ Miklós Simonyi (editor): Problems and Wonders of Chiral Molecules , Akadémiai Kiadó, Budapest, 1990, ISBN 9630558815 .
  3. ^ Hermann J. Roth, Christa E. Müller, Gerd Folkers: Stereochemistry and Drugs , Wissenschaftliche Verlagsgesellschaft Stuttgart, 1998, ISBN 3-8047-1485-4 .
  4. ^ EJ Ariëns: Stereochemistry, a basis for sophisticated nonsense in pharmacokinetics and clinical pharmacology . In: Eur. J. Clin. Pharmacol. . 26, No. 6, 1984, pp. 663-668. PMID 6092093 .