Palladium(0)/indium iodide-mediated allylations of electrophiles generated from the hydrolysis of Eschenmoser’s salt: one-pot preparation of diverse carbocyclic scaffolds

✍ Scribed by Cara Cesario; Marvin J. Miller

• Publisher: Elsevier Science
• Year: 2010
• Tongue: French
• Weight: 327 KB
• Volume: 51
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/j.tetlet.2010.04.007

✦ Synopsis

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.