64878-08-6Relevant articles and documents
Thiol-free chemoenzymatic synthesis of β-ketosulfides
Heredia, Adrián A.,López-Vidal, Martín G.,Kurina-Sanz, Marcela,Bisogno, Fabricio R.,Pe?é?ory, Alicia B.
, p. 378 - 387 (2019/02/20)
A preparation of β-ketosulfides avoiding the use of thiols is described. The combination of a multicomponent reaction and a lipase-catalysed hydrolysis has been developed in order to obtain high chemical diversity employing a single sulfur donor. This methodology for the selective synthesis of a set of β-ketosulfides is performed under mild conditions and can be set up in one-pot two-step and on a gram-scale.
Synthesis of Functionalized β-Keto Arylthioethers by the Aryne Induced [2,3] Stevens Rearrangement of Allylthioethers
Thangaraj, Manikandan,Gaykar, Rahul N.,Roy, Tony,Biju, Akkattu T.
, p. 4470 - 4476 (2017/04/28)
A mild and transition-metal-free synthesis of β-keto arylthioethers has been developed by the aryne triggered [2,3] Stevens rearrangement of allylthioethers. The key sulfur ylide intermediate for the rearrangement was formed by the S-arylation of allylthi
1,4 -S- to O-silyl migration: Multicomponent synthesis of α-thioketones through chemoselective transformation of esters to ketones with organolithium reagents
Sun, Xianwei,Song, Zhenlei,Li, Hongze,Sun, Changzheng
supporting information, p. 17589 - 17594 (2014/01/06)
A [1,4]-S- to O-silyl migration has been exploited to chemoselectively transform esters into ketones by using organolithium reagents, allowing multicomponent synthesis of α-thioketones. Mechanistic studies reveal that this migration proceeds in an intramolecular manner and is more favorable than the corresponding [1,5]-S- to O- and [1,3]-C- to O-silyl migrations. The resulting α-thioketones are valuable building blocks for the synthesis of cyclic or multifunctionalized organosulfur compounds. Productive move: A [1,4]-S- to O-silyl migration has been exploited to chemoselectively transform esters into ketones by using organolithium reagents, allowing the multicomponent synthesis of α-thioketones (see scheme, TMEDA = tetramethylethylenediamine). Mechanistic studies revealed that this migration proceeds in an intramolecular manner and is more favorable than the corresponding [1,5]-S- to O- and [1,3]-C- to O-silyl migrations. The resulting α-thioketones are valuable building blocks for the synthesis of cyclic or multifunctionalized organosulfur compounds.