Chiral Brønsted Acids in the Catalytic Asymmetric Nazarov Cyclization—The First Enantioselective Organocatalytic Electrocyclic Reaction

Magnus Rueping, Winai Ieawsuwan, Andrey P. Antonchick, Boris J. Nachtsheim

Angewandte Chemie International Edition · 2007 · 301 citations · 47 references

Concepts

Abstract

Low catalyst loadings, high enantioselectivities, mild conditions, and fast reaction times are the important features of the first enantioselective organocatalytic electrocyclic reaction: a Nazarov cyclization leading to the synthesis of substituted five-membered rings with a chiral Brønsted acid as a catalyst (see scheme). A further advantage of this method is the possible entry to all four diastereomers of the product.

References

47