Phosphahelicenes in Asymmetric Organocatalysis: [3+2] Cyclizations of γ‐Substituted Allenes and Electron‐Poor Olefins

Maxime Gicquel, Yang Zhang, Paul Aillard, Pascal Retailleau, Arnaud Voituriez, Angéla Marinetti

Angewandte Chemie International Edition · 2015 · 125 citations · 54 references

Concepts

Abstract

The first use of phosphahelicene in enantioselective organocatalysis is reported. New chiral phosphahelicenes have been prepared and enable highly enantioselective [3+2] cyclization reactions between arylidene- or alkylidenemalononitriles and γ-substituted allenoates or cyanoallenes. These reactions afford cyclopentene derivatives in both high yields and diastereoselectivities, with enantiomeric excesses of up to 97 %.

References

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