4.8 Article

Alkynyl Thioethers in Gold-Catalyzed Annulations To Form Oxazoles

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 43, Pages 13310-13313

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201706850

Keywords

cycloaddition; gold; heterocycles; regioselectivity; sulfur

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Non-oxidative, regioselective, and convergent access to densely functionalized oxazoles is realized in a functional-group tolerant manner using alkynyl thioethers. Sulfur-terminated alkynes provide access to reactivity previously requiring strong donor-substituted alkynes such as ynamides. Sulfur does not act in an analogous donor fashion in this gold-catalyzed reaction, thus leading to complementary regioselective outcomes and addressing the limitations of using ynamides.

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