Asymmetric Diels–Alder Reactions of α,β‐Unsaturated Aldehydes Catalyzed by a Diarylprolinol Silyl Ether Salt in the Presence of Water

Yujiro Hayashi, Sampak Samanta, Hiroaki Gotoh, Hayato Ishikawa

Angewandte Chemie International Edition · 2008 · 168 citations · 42 references

Concepts

Abstract

Water, water, everywhere: The title reaction predominantly affords the exo isomer with excellent enantioselectivity (see scheme; TMS=trimethylsilyl). The synthesis can be carried out without organic solvents and provides the products by distillation. Water increases the rate and enantioselectivity of the reaction.

References

42