An efficient and improved synthesis of 1, 5-diketones: versatile conjugate addition of nucleophiles to α, β-unsaturated enones and alkynones

R Shankar, AK Jha, US Singh, K Hajela

Index: Shankar, Ravi; Jha, Ashok K.; Singh, Uma Sharan; Hajela Tetrahedron Letters, 2006 , vol. 47, # 18 p. 3077 - 3079

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Citation Number: 24

Abstract

Several 1, 5-diketones have been prepared in good to excellent yields by versatile conjugate addition of nucleophiles such as cyclic or acyclic ketones, amines and thiols to α, β-unsaturated enones and alkynones, in the presence of catalytic amounts of 10% aq NaOH, TBAI and DMSO at ambient temperature. The choice of solvent and phase-transfer catalyst played a critical role in improving the reaction rate and yields of the products.