61476-94-6Relevant articles and documents
Direct Synthesis of γ-Keto Sulfones from Allylic Alcohols: One-Pot Palladium(II)-Catalyzed Generation of Enones Followed by Water-Mediated 1,4-Addition of Organosulfinates
Vellakkaran, Mari,Andappan, Murugaiah M. S.,Nagaiah, Kommu,Nanubolu, Jagadeesh Babu
supporting information, p. 3575 - 3583 (2016/07/28)
Allylic alcohols were exploited as synthetic precursors of γ-keto sulfones. The reaction involved the one-pot generation of α,β-enones in situ from the allylic alcohols by using a PdII–dioxygen catalytic system and subsequent sulfa-Michael addition in the presence of water. Importantly, water was identified as a sustainable substitute for a toxic copper salt to promote organosulfonyl addition. Diverse examples of aromatic and aliphatic γ-keto sulfones were prepared. Specially, Ar–X (X = Br, Cl) bonds were tolerated, which indicated a chemoselective catalytic system for the preparation of halogen-bearing γ-keto sulfones. This one-pot method does not require an acid, a base, or isolation of any intermediate. Control experiments indicated that the active catalyst of the first step also promoted the subsequent C–S bond-formation reaction. Water was found to accelerate the reaction rate and to be involved in the protonolysis of the σ-alkylpalladium complex, as corroborated by deuterium incorporation.
FeCl3ATMSCl: An effective catalytic system for the conjugate addition of sodium p-toluenesulfinate to αβ-enones
Sreedhar,Reddy, M. Amamath,Reddy, P. Surendra
experimental part, p. 1949 - 1952 (2009/04/10)
A new protocol for the β-sulfonation of αβ-unsaturated carbonyl compounds is described. The method employs FeCl3 as catalyst and TMSC1 as additive for conjugate addition of sodiump-toluenesulfinate to enones.
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.
