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Stereodivergent Catalysis.

Irina P Beletskaya1, Carmen Nájera2, Miguel Yus2

  • 1Chemistry Department , M. V. Lomonosov Moscow State University , Leninskie Gory 1 , 119992 Moscow , Russia.

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Summary

This review explores stereodivergent catalysis, focusing on reactions creating distinct stereoisomers. It covers diverse transformations like additions, functionalizations, and cyclizations using metal and organocatalysts.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Stereoselective Synthesis

Background:

  • Stereodivergent catalysis enables the synthesis of multiple stereoisomers from a single substrate.
  • Controlling stereochemistry is crucial in synthesizing complex molecules, particularly pharmaceuticals.

Purpose of the Study:

  • To provide a comprehensive overview of diastereoselective and enantioselective catalyzed reactions.
  • To highlight the application of metal complexes and organocatalysts in stereodivergent synthesis.

Main Methods:

  • Review of literature on catalyzed reactions in acyclic and cyclic systems.
  • Categorization of reactions including nucleophilic additions, α-functionalization, allylic substitutions, ring openings, alkene synthesis, and cycloadditions.

Main Results:

  • Detailed examination of various stereodivergent reactions, including nucleophilic addition to C=C and C=N bonds.
  • Coverage of α-functionalization of carbonyls, allylic substitutions, and ring opening of epoxides and aziridines.
  • Inclusion of diastereoselective alkene synthesis from alkynes and stereodivergent cycloadditions.

Conclusions:

  • Stereodivergent catalysis offers powerful strategies for accessing diverse stereoisomers.
  • Metal complexes and organocatalysts are versatile tools for achieving high stereocontrol in various organic transformations.