Tetrahedron letters

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

Z Shen, B Li, L Wang, Y Zhang

Index: Shen, Zongxuan; Li, Bin; Wang, Lu; Zhang, Yawen Tetrahedron Letters, 2005 , vol. 46, # 50 p. 8785 - 8788

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Citation Number: 31

Abstract

The aldol-type addition of acetone towards (un) substituted benzoyl, heteroarylcarbonyl or α, β-unsaturated acyl cyanides was efficiently catalyzed by l-proline (30mol%) 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.