Ruthenium Catalyzed C−C Bond Formation via Transfer Hydrogenation: Branch-Selective Reductive Coupling of Allenes to Paraformaldehyde and Higher Aldehydes
- 6 June 2008
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 10 (13) , 2705-2708
- https://doi.org/10.1021/ol800836v
Abstract
Under the conditions of ruthenium-catalyzed transfer hydrogenation employing 2-propanol as the terminal reductant, 1,1-disubstituted allenes 1a−h engage in reductive coupling to paraformaldehyde to furnish homoallylic alcohols 2a−h. Under identical transfer hydrogenation conditions, 1,1-disubstituted allenes engage in reductive coupling to aldehydes 3a−f to furnish homoallylic alcohols 4a−n. In all cases, reductive coupling occurs with branched regioselectivity to deliver homoallylic alcohols bearing all-carbon quaternary centers.Keywords
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