Affiliation:
1. Department of Chemistry and Biochemistry Auburn University 36849 Auburn AL USA
2. Department of Medicinal Chemistry, School of Pharmacy China Pharmaceutical University 210009 Nanjing China
3. Department of Chemistry Virginia Tech 24061 Blacksburg VA USA
Abstract
AbstractWe report herein a Cu‐catalyzed regio‐, diastereo‐ and enantioselective acylboration of 1,3‐butadienylboronate with acyl fluorides. Under the developed conditions, the reactions provide (Z)‐β,γ‐unsaturated ketones bearing an α‐tertiary stereocenter with high Z‐selectivity and excellent enantioselectivities. While direct access to highly enantioenriched E‐isomers was not successful, we showed that such molecules can be synthesized with excellent E‐selectivity and optical purities via Pd‐catalyzed alkene isomerization from the corresponding Z‐isomers. The orthogonal chemical reactivities of the functional groups embedded in the ketone products allow for diverse chemoselective transformations, which provides a valuable platform for further derivatization.
Funder
National Science Foundation
National Institutes of Health
Subject
General Chemistry,Catalysis
Cited by
2 articles.
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