Direct Synthesis of Trisubstituted Isoxazoles through Gold-Catalyzed Domino Reaction of Alkynyl Oxime Ethers

Masafumi Ueda, Aoi Sato, Yuki Ikeda, Tetsuya Miyoshi, Takeaki Naito, Okiko Miyata

Organic Letters · 2010 · 142 citations · 63 references

Concepts

Abstract

Alkynyl oxime ether underwent a gold-catalyzed domino reaction involving cyclization and subsequent Claisen-type rearrangement to afford trisubstituted isoxazoles in a direct, efficient, and regioselective manner. The products were successfully applied to the synthesis of unusual heterocycles as an illustration of the potential utility of the reaction.

References

63