1942-34-3Relevant academic research and scientific papers
Chiral cyclopentadienylruthenium sulfoxide catalysts for asymmetric redox bicycloisomerization
Trost, Barry M.,Ryan, Michael C.,Rao, Meera
, p. 1136 - 1152 (2016)
A full account of our efforts toward an asymmetric redox bicycloisomerization reaction is presented in this article. Cyclopentadienylruthenium (CpRu) complexes containing tethered chiral sulfoxides were synthesized via an oxidative [3 + 2] cycloaddition reaction between an alkyne and an allylruthenium complex. Sulfoxide complex 1 containing a p-anisole moiety on its sulfoxide proved to be the most efficient and selective catalyst for the asymmetric redox bicycloisomerization of 1,6- and 1,7-enynes. This complex was used to synthesize a broad array of [3.1.0] and [4.1.0] bicycles. Sulfonamide- and phosphoramidate-containing products could be deprotected under reducing conditions. Catalysis performed with enantiomerically enriched propargyl alcohols revealed a matched/mismatched effect that was strongly dependent on the nature of the solvent.
C2-symmetric chiral disulfoxide ligands in rhodium-catalyzed 1,4-addition: From ligand synthesis to the enantioselection pathway
Mariz, Ronaldo,Poater, Albert,Gatti, Michele,Drinkel, Emma,Buergi, Justus J.,Luan, Xinjun,Blumentritt, Sascha,Linden, Anthony,Cavallo, Luigi,Dorta, Reto
supporting information; experimental part, p. 14335 - 14347 (2011/03/22)
A family of chiral C2-symmetric disulfoxide ligands possessing biaryl atropisomeric backbones has been synthesized by using the Andersen methodology. Complete characterization includes X-ray crystallographic studies of all ligands and some of t
An efficient and novel method for the synthesis of sulfinate esters under solvent-free conditions
Hajipour, Abdol R.,Falahati, Ali R.,Ruoho, Arnold E.
, p. 2717 - 2719 (2007/10/03)
The present letter describes a reliable one-stage process for the preparation of sulfinate esters from the corresponding sulfinic acid and alcohols in the presence of N,N′-dicyclohexylcarbodiimide (DCC) under solvent-free conditions.
Synthesis of menthyl sulfinate and sulfoxides on solid phase
Rolland, Catherine,Hanquet, Gilles,Ducep, Jean-Bernard,Solladié, Guy
, p. 9077 - 9080 (2007/10/03)
p-Hydroxyphenyl menthyl sulfinate was readily linked to Wang resin. The resulting sulfinate reacted with Grignard reagents and potassium or lithium enolates to give the corresponding sulfoxides or β-ketosulfoxides allowing a study of the chemistry of sulf
An improved and efficient procedure for the preparation of chiral sulfinates from sulfonyl chloride using triphenylphosphine
Watanabe, Yoshihiko,Mase, Nobuyuki,Tateyama, Moto-Aki,Toru, Takeshi
, p. 737 - 745 (2007/10/03)
An improved procedure of the Sharpless method for the preparation of chiral sulfinates by triphenylphosphine is described. A mixture of sulfonyl chlorides and diacetone-D-glucose or l-menthol in the presence of triethylamine was treated with triphenylphos
A convenient and highly diastereoselective synthesis of optically active sulfinate esters from sulfonyl chlorides under solid state conditions
Hajipour, Abdolreza,Islami, Fereshteh
, p. 461 - 462 (2007/10/03)
A manipulatively simple and rapid method for synthesis of chiral sulfinate esters 1 and 2 from sulfonyl chloride and trimethyl phosphite in solid phase conditions supported on silica gel is described. The chemical yields are good to excellent and diastereoselectivity is high.
ASYMMETRIC SYNTHESIS USING ENANTIOMERICALLY PURE 2-(p-ANISYLSULFINYL)-2-CYCLOALKENONES
Posner, Gary H.,Frye, Leah L.,Hulce, Martin
, p. 1401 - 1408 (2007/10/02)
Conjugate additions of many organometallic reagents to 2-(p-anisylsulfinyl)-2-cycloalkenones, 2, proceed with much greater diastereoselectivity than additions to the corresponding 2-(p-tolylsulfinyl)-2-cycloalkenones, 7.Complexation of 2 with zinc dibromide followed by addition of various Grignard reagents lead, after reductive removal of the sulfoxide, to 3-substituted cycloalkanones of higher optical purity than those obtained from 7.Addition of methyltitanium triisopropoxide to 2-(p-anisylsulfinyl)-2-cyclohexenone, 2b, in the absence of zinc dibromide, proceeds with virtually complete asymmetric induction.
