Abstract
The Wittig reaction and related methods for synthesis of C=C double bonds belong to the standard repertoire of the synthetic chemist. Studies of asymmetric versions of these reactions have been increasing in recent years and applications of such processes to complex molecule synthesis have begun to emerge. In this review, we will emphasise the recent advances in developing methods and synthetic applications of these reactions, but earlier results will be covered as well to place the recent results in context.
1 Introduction
2 Reactions with Achiral Monocarbonyl Substrates
2.1 Reactions with Symmetrically Substituted Monoketones
2.2 Synthesis of Chiral Allenes from Ketenes or Acid Halides
3 Reactions with Chiral, Nonracemic Monoketones
4 Kinetic Resolution
4.1 Resolution of Racemic Monocarbonyl Compounds
4.2 Resolution of Racemic Wittig Reagents
5 Dynamic Resolution
6 Other Strategies Based on Resolution of Enantiomers
6.1 Parallel Kinetic Resolution
6.2 Enantioconvergent Synthesis by Sequential Asymmetric HWE Reaction and Palladium-Catalyzed Nucleophilic Allylic Substitution
7 Desymmetrization of Prochiral Dicarbonyl Substrates
8 Future Perspectives, Concluding Remarks
Key words
asymmetric synthesis - asymmetric Wittig reactions - kinetic resolution - enantioconvergent synthesis - desymmetrization
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