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Communication | Special issue | Vol 97, No. 2, 2018, pp.719-728
Published online, 18th May, 2018
DOI: 10.3987/COM-18-S(T)81
Efficient One-Pot Synthesis of Substituted Oxazoles from 3-Trimethylsilylpropargylic Alcohols and Amides by Gold-Catalyzed Substitution Followed by Cycloisomerization

Nobuyoshi Morita,* Aoi Sano, Ayako Sone, Shino Aonuma, Arisa Matsunaga, Yoshimitsu Hashimoto, and Osamu Tamura*

*Laboratory of Organic Chemistry, Pharmaceutical Sciences, Showa Pharmaceutical University, 3-3165, Higashi-tamagawagakuen, Machida, Tokyo 194-8543, Japan

Abstract

3-Trimethylsilylpropargylic alcohols 1, on treatment with amides 2 in the presence of catalytic amounts of cationic gold(III), underwent propargylic substitution followed by cycloisomerization. The key of the cycloisomerization, in which the key feature is the β-cation-stabilizing effect of the silicon atom of 3-trimethylsilyl-propargylic alcohols 1.