86653-05-6Relevant academic research and scientific papers
Sulfone Group as a Versatile and Removable Directing Group for Asymmetric Transfer Hydrogenation of Ketones
Clarkson, Guy J.,Vyas, Vijyesh K.,Wills, Martin
supporting information, p. 14265 - 14269 (2020/07/04)
The sulfone functional group has a strong capacity to direct the asymmetric transfer hydrogenation (ATH) of ketones in the presence of [(arene)Ru(TsDPEN)H] complexes by adopting a position distal to the η6-arene ring. This preference provides a
Catalytic asymmetric conjugate boration of α,β-unsaturated sulfones
Moure, Abraham L.,Gomez Arrayas, Ramon,Carretero, Juan C.
, p. 6701 - 6703 (2011/07/30)
The α,β-unsaturated sulfones are suitable activated olefins in catalytic asymmetric conjugate β-boration. These substrates undergo smooth conjugate addition of bis(pinacolato)diboron [B2(pin)2] catalyzed by nonracemic CuI-diphosphine complexes to provide, upon subsequent oxidation, β-hydroxy sulfones in good yields and high enantiocontrol.
Palladium-catalyzed cascade reaction of α,β-unsaturated sulfones with aryl iodides
Mauleon, Pablo,Nunez, Angel A.,Alonso, Ines,Carretero, Juan C.
, p. 1511 - 1520 (2007/10/03)
Unlike traditionally used acyclic 1,2-disubstituted alkenes, the reaction of α,β-unsaturated phenyl sulfones with aryl iodides under Heck reaction conditions (Pd(OAc)2 as catalyst, Ag2-CO3 as base in DMF at 120°C) takes place mainly by a cascade process, involving one unit of the alkene and three units of the aryl iodide, to afford a substituted 9-phenylsulfonyl-9,10-dihydrophenanthrene, The dominant formation of this 3:1 coupling product, instead of the Heck trisubstituted olefin, shows that aromatic C-H activation processes can compete with the usually fast syn β-hydrogen elimination step in the Heck arylation of an acyclic olefin. The structural scope of this palladium-catalyzed cascade arylation of α,β-unsaturated sulfones has proved to be wide with regard to substitution at the β-position (alkyl, aryl, or alkenyl substitution), substitution at the sulfone unit (alkyl or phenyl sulfones), and configuration at the C=C bond (trans or cis). Moreover, although less favored than in the case of the arylation of α,β-unsaturated sulfones, similarly substituted 9,10-dihydrophenanthrenes have also been obtained in the case of α,β-unsaturated phosphine oxides and α,β-unsaturated phosphonate esters. A Pd0-pdII-pdIV mechanistic pathway involving the successive formation of highly electrophilic σ-alkylpalladium intermediates and palladacycles is proposed for this multi-component arylation.
DIANIONS OF β-HYDROXY SULFONES: NEW AND GENERAL APPROACH TO SELECTIVE SYNTHESIS OF 2(5H)-FURANONES
Tanaka, Kazuhiko,Ootake, Kazuhiko,Imai, Keisuke,Tanaka, Nobuo,Kaji, Aritsune
, p. 633 - 636 (2007/10/02)
Dianions derived from β-hydroxy sulfones are highly reactive toward a variety of electrophiles including alkyl halides, carbonyl compounds, and sodium iodoacetate.A convenient synthetic method for 4-alkyl- and 5-alkyl-2(5H)-furanones has been developed by using these dianions.A new synthetic approach to trans,3,4-bis(3-hydroxybenzyl)dihydro-2(3H)-furanone, the first lignan found in humans, via a facile reduction of 2(5H)-furanone with Mg-methanol is also described.
