4-Isopropyl-2-oxazolin-5-one anion as masked umpoled synthon for both formyl and hydroxycarbonyl anions: Generation, reactivity and synthetic applications

…, S Benetti, C De Risi, GP Pollini, G Spalluto, V Zanirato

Index: Barco, Achille; Benetti, Simonetta; De Risi, Carmela; Pollini, Gian P.; Spalluto, Giampiero; Zanirato, Vinicio Tetrahedron, 1996 , vol. 52, # 13 p. 4719 - 4734

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Citation Number: 14

Abstract

The anion of the title compound, simply generated in the presence of catalytic amount of triethylamine, reacts with both common electrophilic olefins and aldehydes to give moderate to good yield of Michael or aldol adducts respectively. Mild acid treatment of these adducts at ambient temperature serves to demask the aldehyde function, allowing one to consider the anion of 1 as a nucleophilic acylating equivalent of formaldehyde. On the other hand, ...