226709-30-4

Upstream product

• 631-67-4 N,N-dimethylthioacetamide 
• 220972-34-9 1,2:5,6-di-O-isopropylidene-α-D-glucofuranosyl (S)-cyclohexanesulfinate 
• 188055-05-2 Methyl 4-fluorophenyl trithiocarbonate 
• 41719-04-4 Cyclohexanesulfinyl chloride 
• 124-40-3 dimethyl amine 

Downstream Products

• 385837-68-3 (SS)-1-[(Z)-but-2-enylsulfanyl]-2-(cyclohexylsulfinyl)-1-(N,N-dimethylamino)-(Z)-ethene 
• 385837-66-1 (SS)-1-[(E)-but-2-enylsulfanyl]-2-(cyclohexylsulfinyl)-1-(N,N-dimethylamino)-(Z)-ethene 
• 385837-74-1 (SS)-2-(cyclohexylsulfinyl)-1-(N,N-dimethylamino)-1-[(Z)-1-phenylpropenylsulfanyl]-(Z)-ethene 
• 385837-96-7 (S)-2-(cyclohexylsulfinyl)-1-(N,N-dimethylamino)-1-(prop-2-enylsulfanyl)-(Z)-ethene 
• 385837-71-8 (SS)-2-(cyclohexylsulfinyl)-1-(N,N-dimethylamino)-1-[(E)-1-phenylpropenylsulfanyl]-(Z)-ethene 
• 385838-00-6 (S)-1-(2-bromoprop-2-enylsulfanyl)-2-(cyclohexylsulfinyl)-1-(N,N-dimethylamino)-(Z)-ethene 
• 385837-76-3 (SS,2S,3R)-2-cyclohexylsulfinyl-N,N-dimethyl-3-methylpent-4-enethioamide 
• 385837-77-4 (SS,2S,3S)-2-cyclohexylsulfinyl-N,N-dimethyl-3-phenylpent-4-enethioamide 
• 670223-09-3 (3S,5R)-4,5-dihydro-3-cyclohexylsulfanyl-5-iodomethyl-2(3H)-furanone 
• 670223-05-9 (S)-2-cyclohexylsulfanyl-N,N-dimethylpent-4-enamide 
• 670223-06-0 (SS,2S)-2-cyclohexylsulfinyl-N,N-dimethylpent-4-enamide 

Relevant academic research and scientific papers

Asymmetric induction by a sulfinyl group in the thio-Claisen rearrangement

The first examples of an asymmetric thio-Claisen rearrangement induced by an enantiopure alkylsulfinyl group are reported.

Asymmetric thio-claisen rearrangement induced by an enantiopure alkylsulfinyl group. Unusual preference for a boat transition state in the acyclic series

Ketene aminothioacetals 2a-c and 5a-b bearing an enantiopure vinylic alkylsulfinyl substituent were readily prepared from (R)-2-cyclohexylsulfinyl-N,N-dimethylethanethioamide 1 with full control of the geometry of their double bonds. They underwent a Claisen rearrangement upon heating at THF reflux to afford α-sulfinyl ?-unsaturated thioamides 3a-c and 6a-b. With all substrates the asymmetric induction of the sulfinyl group was excellent. The determination of the absolute configurations of thioamides 3a-c and 6a-b was achieved either by X-ray crystallographic analysis or by chemical correlation. The stereochemical course of this [3,3] sigmatropic transposition was explained by an electronic model. Interestingly the Claisen rearrangement of the (ZE)-cinnamyl substrates 5b was shown to proceed through a boat transition state rather than a chair transition state; such a preference is quite unusual for acyclic systems.

Synthesis of racemic and enantiopure 2-alkylsulfinyl dithioacetates and thioacetamides

New 2-alkylsulfinyl dithioacetates and thioacetamides have been prepared. The asymmetric synthesis of (R)-2-(cyclohexylsulfinyl)-N,N- dimethylthioacetamide from previously unreported (S)-diacetone-D-glucose cyclohexanesulfinate was achieved in excellent y