A Borate Propeller Compound as Chiral Catalyst for an Asymmetrically Induced Diels‐Alder Reaction

Dieter Kaufmann, Roland Boese

Angewandte Chemie International Edition in English · 1990 · 99 citations · 4 references

Concepts

Abstract

Three binaphthyl groups as “blades” have been joined together to give the propeller compound 1. The synthesis of this compound proved surprisingly easy via reaction of a borane with optically active 1,1′-bi-2-naphthol. Compound 1 is more than just “a cute molecule”; it also catalyzes a highly exo and enantioselective Diels–Alder reaction of cyclopentadiene with methacrolein.

References

4