Regio‐ and Enantioselective Rhodium‐Catalyzed Addition of 1,3‐Diketones to Allenes: Construction of Asymmetric Tertiary and Quaternary All Carbon Centers

Thorsten M. Beck, Bernhard Breit

Angewandte Chemie · 2017 · 41 citations · 70 references

Concepts

Abstract

Abstract An unprecedented highly regio‐ and enantioselective rhodium‐catalyzed addition of 1,3‐diketones to terminal and 1,1‐disubstituted allenes furnishing asymmetric tertiary and quaternary all‐carbon centers is reported. By applying a Rh I /phosphoramidite/TFA catalytic system under mild conditions, the desired chiral branched α‐allylated 1,3‐diketones could be obtained in good to excellent yields, with perfect regioselectivity and in high enantioselectivity. The reaction shows a broad functional‐group tolerance on both reaction partners highlighting its synthetic potential.

References

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