Organoaluminum-Mediated Interrupted Nazarov Reaction†
Yonghoon Kwon
Department of Chemistry, University of Alberta, E3-43 Gunning-Lemieux Chemistry Centre, Edmonton, Alberta, T6G 2G2 (Canada)
Search for more papers by this authorDr. Robert McDonald
X-ray Crystallographic Lab, Department of Chemistry, University of Alberta (Canada)
Search for more papers by this authorCorresponding Author
Prof. Frederick G. West
Department of Chemistry, University of Alberta, E3-43 Gunning-Lemieux Chemistry Centre, Edmonton, Alberta, T6G 2G2 (Canada)
Department of Chemistry, University of Alberta, E3-43 Gunning-Lemieux Chemistry Centre, Edmonton, Alberta, T6G 2G2 (Canada)Search for more papers by this authorYonghoon Kwon
Department of Chemistry, University of Alberta, E3-43 Gunning-Lemieux Chemistry Centre, Edmonton, Alberta, T6G 2G2 (Canada)
Search for more papers by this authorDr. Robert McDonald
X-ray Crystallographic Lab, Department of Chemistry, University of Alberta (Canada)
Search for more papers by this authorCorresponding Author
Prof. Frederick G. West
Department of Chemistry, University of Alberta, E3-43 Gunning-Lemieux Chemistry Centre, Edmonton, Alberta, T6G 2G2 (Canada)
Department of Chemistry, University of Alberta, E3-43 Gunning-Lemieux Chemistry Centre, Edmonton, Alberta, T6G 2G2 (Canada)Search for more papers by this authorWe thank NSERC for support of this work.
Graphical Abstract
InternAl delivery: Organoaluminum reagents activate 1,4-dien-3-ones for Nazarov electrocyclization (see scheme), then transfer a substituent to the resulting cyclopentenyl cation with moderate to complete regioselectivity and diastereoselectivity.
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References
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