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Ketalised α- and β-lithiated α,β-unsaturated ketones: New masked acylvinyl anion equivalents

✍ Scribed by Abderrazak Bachki; Francisco Foubelo; Miguel Yus

Book ID: 104207709
Publisher: Elsevier Science
Year: 1997
Tongue: French
Weight: 889 KB
Volume: 53
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(97)00187-7

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✦ Synopsis

The reaction of chloroketals 1, 5 and 10 with an excess of lithium powder and a catalytic amount of DTBB (4-5%) in THF at -78 or -90°C leads to the corresponding functionalised organolithium compounds 2, 6 and l 1, respectively, resulting from a chlorine/lithium exchange; treatment of these intermediates with different electrophiles [H20, D20, Me3SiCI, ButCHO, PhCHO, Me2CO, (CH2)4CO, (CH2)5CO, PhCOMe] affords, after hydrolysis with water, the corresponding products 3, 7 and 12, respectively. Careful acidic hydrolysis of these ketalised products with a 10% aqueous solution of oxalic acid leads to the expected ketones 4, 9 and 13, respectively.

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