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ChemInform Abstract: Ketalized α- and β-Lithiated α,β-Unsaturated Ketones: New Masked Acylvinyl Anion Equivalents.

✍ Scribed by A. BACHKI; F. FOUBELO; M. YUS

Book ID
101850694
Publisher
John Wiley and Sons
Year
2010
Weight
38 KB
Volume
28
Category
Article
ISSN
0931-7597

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✦ Synopsis

Ketalized α-and β-Lithiated α,β-Unsaturated Ketones: New Masked Acylvinyl Anion Equivalents.

-The reaction of chloroketals with lithium in the presence of di-tert-butylbiphenyl as catalyst gives the corresponding intermediate lithiated compounds, which afford with various electrophiles (H2O, D2O, Tms-Cl, aldehydes, ketones) after hydrolysis the corresponding functionalized products. Careful deprotection under mild conditions B) leads to the expected ketones, e.g. (IV), (VII), and (XII). For the reaction of chiral ketals (VIII) and (XIII) with prochiral pivalaldehyde (IIa) no asymmetric induction is observed. -(BACHKI, A.;

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