Contemporaneous Dual Catalysis: Aldol Products from Non-Carbonyl Substrates.
The aldol reaction represents an important class of atom-economic carbon-carbon bond-forming reactions vital to modern organic synthesis. Despite the attention this reaction has received, issues related to chemo- and regioselectivity as well as reactivity of readily enolizable electrophiles remain. To help overcome these limitations, a new direct approach toward aldol products that does not rely upon carbonyl substrates is described. This approach employs room-temperature contemporaneous lanthanum/vanadium dual catalysis, whereby a vanadium-catalyzed 1,3-transposition of allenols is coupled with a lanthanum-catalyzed Meinwald rearrangement of epoxides in situ to directly form aldol products.
Department of Chemistry, Stanford University, Stanford, CA 94305 (USA). bmtrost@stanford.edu.
Barry M
BM
Trost
Department of Chemistry, Stanford University, Stanford, CA 94305 (USA).
Jacob S
JS
Tracy
aldol reaction; contemporaneous dual catalysis; lanthanum; rearrangement; vanadium