2642-99-1Relevant academic research and scientific papers
Chiral cyclopentadienylruthenium sulfoxide catalysts for asymmetric redox bicycloisomerization
Trost, Barry M.,Ryan, Michael C.,Rao, Meera
, p. 1136 - 1152 (2016/07/06)
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.
A chiral sulfoxide-ligated ruthenium complex for asymmetric catalysis: Enantio- and regioselective allylic substitution
Trost, Barry M.,Rao, Meera,Dieskau, Andre P.
supporting information, p. 18697 - 18704 (2014/01/06)
The design and synthesis of a novel chiral sulfoxide-ligated cyclopentadienyl ruthenium complex is described. Its utility as an asymmetric variant of [CpRu(MeCN)3]PF6 is demonstrated through its ability to function in the branched-selective asymmetric allylic alkylation of phenols and carboxylic acids. Water has also been shown to act as a competent nucleophile in this reaction to generate branched allyl alcohols with good regio- and enantioselectivities.
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
Asymmetric Induction during Organometallic Conjugate Addition to Enantiomerically Pure 2-(Arylsulfinyl)-2-cyclopentenones
Posner, Gary H.,Mallamo, John P.,Hulce, Martin,Frye, Leah L.
, p. 4180 - 4185 (2007/10/02)
Virtually complete asymmetric induction is achieved during methyl-, vinyl- and naphthylmetallic conjugate addition to enantiomerically pure (S)-(+)-2-(p-tolylsulfinyl)-2-cyclopentenone ((S)-(+)-1). (R)-3-Methylcyclopentanone is obtained when the enone sul
