91923-30-7

Upstream product

• 4630-82-4 methyl cyclohexylcarboxylate 
• 2812-72-8 methyl chlorothioformate 

Downstream Products

• 63822-79-7 O-(2-(2-hydroxyethoxy)ethyl) cyclohexanecarbothioate 
• 1415241-07-4 cyclohexanecarboselenothioic acid Se-2-(trimethylsilyl)ethyl ester 
• 1415241-23-4 cyclohexanecarboselenothioic acid Se-methyl ester 
• 1415241-22-3 tetrabutylammonium cyclohexanecarboselenothioate 

Relevant academic research and scientific papers

Base-Catalyzed Transesterification of Thionoesters

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.

An Expeditious Route to trans-Configured Tetrahydrothiophenes Enabled by Fe(OTf)3-Catalyzed [3+2] Cycloaddition of Donor–Acceptor Cyclopropanes with Thionoesters

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.

A CONVENIENT SYNTHESIS OF O-ALKYL THIOESTERS FROM ESTERS

O-Alkyl thioesters may be prepared from the corresponding carboxylic esters by successive treatment with lithium diisopropylamide, chlorotrimethylsilane, and hydrogen sulfide.