167902-86-5Relevant articles and documents
Lithiated 3-Tosylpropanal and 4-Tosyl-2-butanone Dimethyl Acetals as β-Acylvinyl Anion Equivalents for the Synthesis of Unsaturated 1,4-Dicarbonyl Compound and α,β-Butenolides
Bonete, Pedro,Najera, Carmen
, p. 2763 - 2776 (2007/10/02)
The lithiation of 1,1-dimethoxy-3-tosyllpropane (7a) and 2,2-dimethoxy-4-tosylbutane (7b) followed by reaction with acyl chlorides affords, after p-toluenesulfinic acid elimination, ene-1,4-dicarbonyl compounds in a stereoselective manner.In the case of compound 7a, derived from acrolein, sequential monolithiation and reaction with carbonyl compounds give cyclic acetals, which after oxidation and elimination of p-toluenesulfinic acid are transformed into α,β-butenolides.
Lithium 3-lithio-3-tosylpropanoate: A useful α-tosylated homoenolate anion
Bonete,Najera
, p. 4065 - 4068 (2007/10/02)
Lithium 3-lithio-3-tosylpropanoate prepared by dilithiation of 3-tosylpropanoic acid with n-butyllithium at -78°C, reacts with different electrophiles yielding the expected 3-functionalized tosylated propanoic acids. When carbonyl compounds are used as electrophiles the corresponding α,β-butenolides are prepared directly.
