Proline-catalyzed aldol reactions of acyl cyanides with acetone: An efficient and convenient synthesis of 1,3-diketones

Document Type

Article

Publication Date

12-12-2005

Abstract

The aldol-type addition of acetone towards (un)substituted benzoyl, heteroarylcarbonyl or α,β-unsaturated acyl cyanides was efficiently catalyzed by l-proline (30 mol %) to give 2-hydroxy-4-oxo-2-substituted pentanenitriles. Upon the treatment with sodium hydroxide, the adducts transformed to 1,3-diketones in good-to-excellent yield, furnishing an efficient and convenient method for the regioselective synthesis of 1,3-diketones. © 2005 Elsevier Ltd. All rights reserved.

Publication Source (Journal or Book title)

Tetrahedron Letters

First Page

8785

Last Page

8788

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