1942-34-3Relevant articles and documents
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.
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.
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