Palladium(0)/indium iodide-mediated allylations of electrophiles generated from the hydrolysis of Eschenmoser's salt: One-pot preparation of diverse carbocyclic scaffolds.
A formyl equivalent was generated in situ from Eschenmoser's salt in aqueous THF and was reacted with an allylindium species. Acylnitroso-derived hetero-Diels Alder adducts and related allyl acetates were shown to be substrates for Pd(0)/InI-mediated allylations of formaldehyde-related species to provide homoallylic alcohols. Hydroxymethyl groups were installed with regio- and diastereocontrol to provide relevant disubstituted carbocyclic scaffolds. Enantiopure anti-disubstituted cyclopentene products were prepared from a chiral allyl acetate.
University of Notre Dame, Department of Chemistry and Biochemistry, 251 Nieuwland Science Hall, Notre Dame, Indiana 46556.
Cara
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Cesario
Marvin J
MJ
Miller