ChemInform Abstract: Behavior of Dioxolanones as Chiral Acyl Anion Equivalents.

✍ Scribed by R. A. AITKEN; A. W. THOMAS

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 35 KB
• Volume: 29
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199819125

✦ Synopsis

Behavior of Dioxolanones as Chiral Acyl Anion Equivalents.

-Deprotonation of 1,3-dioxolan-4-ones [cf. (I)] and following alkylation gives products (III). Their flash vacuum pyrolysis yields ketones (IV) (with concomitant loss of CO and acetone) showing (I) to be acyl anion equivalents. Conjugate addition of the anion to ethyl crotonate similarly gives β-methyl-γ-oxo esters (VIII). Using chiral dioxolanones these can be obtained in up to 86% e.e. -