1073-29-6Relevant articles and documents
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Minato,H. et al.
, p. 701 - 706 (1975)
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Iodine-Mediated Synthesis of Methylthio-Substituted Catechols from Cyclohexanones
Wu, Yue-Hua,Wang, Nai-Xing,Zhang, Tong,Yan, Zhan,Xu, Bao-Cai,Inoa, Joan,Xing, Yalan
supporting information, p. 3008 - 3013 (2019/04/30)
A novel and efficient I2-mediated direct synthesis of methylthio-substituted catechols from cyclohexanones was developed. Various cyclohexanones underwent oxygenation, methylthiolation, and dehydrogenative aromatization in one pot to form the desired products in moderate to good yields. DMSO was utilized as the solvent, oxygen source, and methylthiolation agent. A possible reaction mechanism is proposed. (Figure presented.).
Biocatalytic Preparation of Chiral Sulfoxides through Asymmetric Reductive Resolution by Methionine Sulfoxide Reductase A
Peng, Liaotian,Wen, Yuanmei,Chen, Yu,Yuan, Zhimei,Zhou, Yang,Cheng, Xiaoling,Chen, Yongzheng,Yang, Jiawei
, p. 3284 - 3290 (2018/06/04)
Here we report an environmentally friendly method for the preparation of chiral sulfoxides under high substrate concentration using recombinant methionine sulfoxide reductase A from Pseudomonas monteilii (pmMsrA) as a biocatalyst. Our results show that this enzyme can effectively accomplish the preparation of (R)-sulfoxides with approximately 50 % yield and 94–99 % enantiomeric excess through asymmetric reductive resolution of racemic sulfoxide. With the establishment of the enzyme regeneration system, the initial substrate concentration could be increased 40–100 times compared to our original report. The (R)-sulfoxides were obtained with high enantioselectivity under the substrate concentration up to 200 mm (approximately 32 g L?1), representing a quite high substrate concentration in biocatalytic preparation of chiral sulfoxides. Moreover, this system showed fairly good activity and enantioselectivity towards a series of ortho- and para-substituted phenyl methyl sulfoxides under high substrate concentration.
Chemoenzymatic synthesis of enantiopure hydroxy sulfoxides derived from substituted arenes
Boyd, Derek R.,Sharma, Narain D.,Malone, John F.,Ljubez, Vera,Murphy, Deirdre,Shepherd, Steven D.,Allen, Christopher C. R.
, p. 2651 - 2664 (2016/03/05)
Enantiopure β-hydroxy sulfoxides and catechol sulfoxides were obtained, by chemoenzymatic synthesis, involving dioxygenase-catalysed benzylic hydroxylation or arene cis-dihydroxylation and cis-diol dehydrogenase-catalysed dehydrogenation. Absolute configurations of chiral hydroxy sulfoxides were determined by X-ray crystallography, ECD spectroscopy and stereochemical correlation. The application of a new range of β-hydroxy sulfoxides as chiral ligands was examined.
