66536-76-3Relevant 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
Formation of single diastereomers of β-hydroxy-sulfoxides by biotransformation of β-ketosulfides using Helminthosporium species NRRL 4671
Holland, Herbert L.,Ihasz, Nancy,Lounsbery, Brendan J.
, p. 640 - 642 (2007/10/03)
Single biotransformations of 1-(phenylthio)-2-propanone and 1-(p-methoxyphenylthio)-2-propanone by the fungus Helminthosporium species NRRL 4671 resulted in both sulfur oxidation to the sulfoxide and carbonyl reduction to the alcohol. The corresponding (SS,SC)-1-sulfinyl-2-propanols were obtained as single diastereomers following simple crystallization.
Humicola lanuginosa lipase-catalyzed enantioselective resolution of β-hydroxy sulfides: Versatile synthons for enantiopure β-hydroxy sulfoxides
Singh, Satwinder,Kumar, Subodh,Chimni, Swapandeep Singh
, p. 2457 - 2462 (2007/10/03)
Humicola lanuginosa lipase-catalyzed acylation of β-hydroxy sulfides provides both the (R)- and (S)-enantiomers in high enantiomeric purity. In two cases the resolved hydroxy sulfides were oxidized to give β-hydroxy sulfoxides in >99% e.e. The effect of substituents on enantioselectivity is discussed.
Effect of Intramolecular Chelation on Configurational Interconversion of Sulphur-stabilized Carbanions
Tanikaga, Rikuhei,Hamamura, Kazumasa,Hosoya, Ken,Kaji, Aritsune
, p. 817 - 818 (2007/10/02)
Sulphur-stabilized carbanions R1R2-SO undergo configurational interconversion, which is affected by intramolecular chelation and the bulk of R.
Switching of the Direction of Enzyme-Mediated Oxidation and Reduction of Sulfur-Substituted 2-Propanols and 2-Propanones
Ohta, Hiromichi,Kato, Yasuo,Tsuchihashi, Gen-ichi
, p. 2735 - 2739 (2007/10/02)
Incubation of 1-(phenylsulfenyl)-2-propanone with Corynebacterium equi IFO 3730 grown on hexadecane at pH 6.5 afforded the corresponding 1-substituted S propanols. 1-(Phenylsulfinyl)-2-propanone was also reduced by the microorganism, the product being aff
DIASTEREOSELECTIVE α-ALKYLATION OF β-HYDROXY SULFOXIDES AND ITS APPLICATION TO THE SYNTHESIS OF (+)- AND (-)-DISPARLURE
Sato, Toshio,Itoh, Takatoshi,Fujisawa, Tamotsu
, p. 5677 - 5680 (2007/10/02)
α-Alkylation of the dianions of β-hydroxy sulfoxides proceeds with high 1,2-asymmetric induction to give threo-α-alkyl-β-hydroxy sulfoxides.The utility of the present reaction was demonstrated in the asymmetric synthesis of (+)- and (-)-cis-7,8-epoxy-2-methyloctadecanes (disparlure).
