GaCl3-Catalyzed Ring-Opening Carbonyl–Olefin Metathesis

• DOI: 10.1021/acs.orglett.8b02086
• Publication Date: 2018-07-27T18:19:41Z
• Authors: Haley Albright; Hannah L. Vonesh; Marc R. Becker; Brandon W. Alexander; Jacob R. Ludwig; Ren A. Wiscons; Corinna S. Schindler
• Keywords: Cycloparaffins; Gallium; Stereoisomerism; Alkenes; Ketones; 01 natural sciences; Catalysis; Lewis Acids; 0104 chemical sciences

The development of a Lewis acid-catalyzed ring-opening cross-metathesis reaction which enables selective access to acyclic, unsaturated ketones as the carbonyl-olefin metathesis products is described. While catalytic amounts of FeCl3 were previously identified as optimal to catalyze ring-closing metathesis reactions, the complementary ring-opening metathesis between cyclic alkenes and carbonyl functionalities relies on GaCl3 as the superior Lewis acid catalyst.