Direct generation of lithium homoenolates from 3-aryl α,β-unsaturated ketones or esters by an arene-catalysed lithiation: Synthesis of substituted tetrahydrofurans and γ-butyrolactones

✍ Scribed by Emma Alonso; Diego J. Ramón; Miguel Yus

• Book ID: 104207507
• Publisher: Elsevier Science
• Year: 1997
• Tongue: French
• Weight: 644 KB
• Volume: 53
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(96)01155-6

✦ Synopsis

The reaction of ct,13-unsaturated ketones 1 with an excess of lithium powder, a catalytic amount of naphthalene (4 %) and different carbonyl compounds in the presence of boron trifluoride in THF at -78 -0°C yields, after treatament with silyl nucleophile and final hydrolysis, the expected substituted tetrahydrofurans 5. Similar methodology applied to ~-aryl acrylic esters 6, but without using boron lrifluoride or silyl reagents yields the corresponding lactones 7.