118204-67-4Relevant academic research and scientific papers
Chemoenzymatic synthesis of β-hydroxyl-sulfoxides by a two-step reaction of enzymatic reduction using Pseudomonas monteilii species and sulfoxidation with chiral titanium complexe
Cui, Baodong,Yang, Min,Shan, Jing,Qin, Lei,Liu, Ziyan,Wan, Nanwei,Han, Wenyong,Chen, Yongzheng
, p. 5200 - 5206 (2017/07/28)
A two-step enantioselective synthetic strategy for the preparation of β-hydroxyl-sulfoxides has been described. With the enzymatic reduction of β-ketosulfides using Pseudomonas monteilii ZMU-T04 followed by the asymmetric sulfoxidation with Ti(OiPr)4/(S)-BINOL complexe, a wide range of corresponding β-hydroxyl-sulfoxide derivatives were smoothly obtained with excellent stereoselectivities (up to 99:1 dr and >99% ee). A plausible chelate structure of titanium complexe in the asymmetric sulfoxidation of β-hydroxyl-sulfides was also proposed on the basis of control experiments.
A chemo-enzymatic synthesis of chiral secondary alcohols bearing sulfur-containing functionality
Chen, Qihui,Wang, Ke,Yuan, Chengye
experimental part, p. 972 - 975 (2010/08/21)
A facile method for the preparation of chiral secondary alcohols bearing a sulfur-containing functionality using a chemo-enzymatic approach is described, with the aid of baker's yeast and Candida Antarctica lipase B. A complete set of four stereoisomers o
A General Method for the Synthesis of Both Enantiomers of Optically Pure β-Hydroxy Esters from (S)-(p-Chlorophenylsulfinyl)acetone Easily Obtainable by Kinetic Resolution with Bakers' Yeast
Fujitsawa, Tamotsu,Fujimura, Atsushi,Sato, Toshio
, p. 1273 - 1280 (2007/10/02)
Both enantiomers of various optically pure (R)- and (S)-β-hydroxy esters were generally synthesized from (S)-(p-chlorophenylsulfinyl)acetone obtained by kinetic resolution with bakers' yeast, followed by γ-alkylation, diastereoselective reduction, subsequent introduction of ester group and reductive elimination of the sulfinyl group.The key step of the diastereoselective reduction of (S)-β-keto sulfoxides was performed with diisobutylaluminum hydride to give (R)C-(S)S-β-hydroxy sulfoxides or after complexation with zinc chloride followed by addition of diisobutylaluminum hydride to give (S)C-(S)S-β-hydroxy sulfoxides which were easily separated in an optically pure form by easy crystallization or separation by silica-gel chromatography due to the p-chlorophenyl moiety in the β-hydroxy sulfoxides.The utility of the present method could be successfully demonstrated in the synthesis of both (+)- and (-)-corynomycolic acids from optically pure methyl esters of (R)- and (S)-3-hydroxyoctadecanoic acid by alkylation with tetradecyl iodide at α-position and hydrolysis.
