40669-41-8Relevant academic research and scientific papers
An Expeditious Route to trans-Configured Tetrahydrothiophenes Enabled by Fe(OTf)3-Catalyzed [3+2] Cycloaddition of Donor–Acceptor Cyclopropanes with Thionoesters
Matsumoto, Yohei,Nakatake, Daiki,Yazaki, Ryo,Ohshima, Takashi
supporting information, p. 6062 - 6066 (2018/03/28)
A synthetic route to trans-configured tetrahydrothiophenes (THTs) through Fe(OTf)3-promoted [3+2] cycloaddition of donor–acceptor cyclopropanes with thionoesters was developed. The cycloaddition proceeded in high yield with high diastereoselectivity, affording transient α-alkoxy THTs. Not only aromatic and aliphatic thionoesters, but also thionolactone were applicable to the present iron catalysis. Further transformation of the S,O-ketal functionality of the product was achieved in a highly trans diastereoselective manner. Moreover, the utility of our methodology was clearly demonstrated by the synthesis of enantioenriched trans-configured THTs.
Base-Catalyzed Transesterification of Thionoesters
Newton, Josiah J.,Britton, Robert,Friesen, Chadron M.
, p. 12784 - 12792 (2018/10/20)
Here we report a convenient synthesis of thionoesters by base-catalyzed transesterification. Benzyl and alkyl thionobenzoates and thionoheterobenzoates were efficiently prepared using various alcohols catalyzed by the corresponding sodium alkoxide. This methodology features a broad substrate scope, good to excellent yields, short reaction times, while simultaneously driving the reaction toward completion through the removal of the methanol byproduct. We also report the conversion of a small collection of thionobenzoates into the corresponding α,α-difluorobenzyl ethers to demonstrate the conversion of alcohols into difluorobenzyl or difluoroheterobenzyl ethers, a process that could prove useful for lead optimization in medicinal chemistry.
Compositions and methods for thionation during chemical synthesis reactions
-
, (2008/06/13)
Compositions and methods for using these compositions to produce high yields of thionated compounds are provided.
Thionation of esters and lactones with the reagent combination of phosphorus pentasulfide and hexamethyldisiloxane
Curphey, Thomas J
, p. 371 - 373 (2007/10/03)
The combination of P4S10 and hexamethyldisiloxane converts esters and lactones to thionoesters and thionolactones in yields comparable to or superior to those obtained with Lawesson's reagent. The method has the advantage that reagent-derived byproducts may be removed by a simple hydrolytic workup or by filtration through silica gel, rather than by chromatography, as required for Lawesson's reagent.
Thionation with the reagent combination of phosphorus pentasulfide and hexamethyldisiloxane
Curphey, Thomas J.
, p. 6461 - 6473 (2007/10/03)
The combination of P4S10 and hexamethyldisiloxane efficiently converts esters, lactones, amides, lactams, and ketones to their corresponding thiono derivatives. In the presence of elemental sulfur, 3-oxoesters are converted to dithiolethiones by this reagent. Yields are comparable to or superior to those obtained with Lawesson's reagent. The method has the advantage that reagent-derived byproducts may be removed by a simple hydrolytic workup or by filtration through silica gel, rather than by chromatography, as required for Lawesson's reagent.
A New, Efficient Synthesis of Thioloesters
Nowicki, Tomasz,Markowska, Anna,Kielbasinski, Piotr,Mikolajczyk, Marian
, p. 305 - 308 (2007/10/02)
The reaction between phosphorothioic and thiocarboxylic acids and O-alkyl-N,N-dicyclohexylisoureas has been found to give the corresponding phosphorothiolates and thiolocarboxylates in high yields (65-95percent), providing a new method for the thiophosphorylation and thiocarboxylation of alcohols.
New Conversion of Esters to Ethers and Its Application to the Preparation of Furano-18-crown-6
Baxter, Steven L.,Bradshaw, Jerald S.
, p. 831 - 832 (2007/10/02)
Thionoesters which are readily prepared from esters can be desulfurized with Raney nickel to form the corresponding ethers.This new synthetic pathway to convert esters to ethers avoids many of the steric and functional limitations of known methods and appears to be a general method for this conversion.
