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Enantioselective Allylation Using Allene, a Petroleum Cracking Byproduct

Richard Y. Liu, Yujing Zhou, Yang Yang, Stephen L. Buchwald*

*Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States, Email:

R. Y. Liu, Y. Zhou, Y. Yang, S. L. Buchwald, J. Am. Chem. Soc., 2019, 141, 2251-2256.

DOI: 10.1021/jacs.8b13907 (free Supporting Information)

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The combination of allene gas with inexpensive and environmentally benign hydrosilanes enables enantioselective ketone allylation reactions without stoichiometric quantities of an allylmetal reagent. This process is catalyzed by copper salts and commercially available ligands, operates without specialized equipment or pressurization, and tolerates a broad range of functional groups.

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Key Words

homoallylic alcohols, dimethoxy(methyl)silane

ID: J48-Y2019