Palladium-Catalyzed Functionalization of Olefins and Alkynes: From Oxyalkynylation to Tethered Dynamic Kinetic Asymmetric Transformations (DYKAT)

Abstract

This review presents an account of the palladium-catalyzed functionalizations of alkenes and alkynes developed at the Laboratory of Catalysis and Organic Synthesis (LCSO). Starting from the intramolecular oxy- and aminoalkynylation of alkenes, tethered methods were then developed to functionalize allylic amines and alcohols, as well as propargylic amines. Finally, a new dynamic kinetic asymmetric transformation was developed based on the use of a ‘one-arm’ Trost-type ligand, giving access to enantiopure amino alcohols. Each section is a personal account by the researcher(s) who performed the work.

1 Introduction,

2 Oxy- and Aminoalkynylation of Olefins,

3 In Situ Tethering Strategies for the Synthesis of Vicinal Amino Alcohols and Diamines,

4 Carboamination of Allylic Alcohols,

5 Carbooxygenation of Propargylic Amines,

6 Enantioselective Carboetherification/Hydrogenation via a Catalytically Formed Chiral Auxiliary,

7 Conclusion

Key words

synthetic methods - palladium catalysis - alkynes - Trost ligands - DYKAT

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