385837-48-9

Upstream product

• 106-95-6 allyl bromide 
• 226709-30-4 (R)-2-(Cyclohexylsulfinyl)-N,N-dimethylethanethioamide 
• 385837-96-7 (S)-2-(cyclohexylsulfinyl)-1-(N,N-dimethylamino)-1-(prop-2-enylsulfanyl)-(Z)-ethene 

Downstream Products

• 670223-06-0 (SS,2S)-2-cyclohexylsulfinyl-N,N-dimethylpent-4-enamide 
• 890706-45-3 3-cyclohexanesulfinyl-5-methyl-dihydro-furan-2-one 
• 890706-52-2 (5S)-3-cyclohexylsulfanyl-5-methyl-5H-furan-2-one 
• 890706-54-4 (5S)-3-cyclohexylsulfanyl-5-ethyl-dihydrofuran-2-one 
• 890706-57-7 (5S)-3-cyclohexylsulfanyl-5-ethyl-5-H-furan-2-one 
• 890706-53-3 methyl (4R)-2-cyclohexylsulfanyl-3-oxiranylpropanoate 
• 890706-58-8 (5S)-3-cyclohexanesulfinyl-5-ethyl-5-H-furan-2-one 
• 890706-46-4 3-cyclohexanesulfinyl-5-methyl-3-phenylselanyl-dihydro-furan-2-one 
• 890706-49-7 3-cyclohexanesulfinyl-5-iodomethyl-3-phenylselanyl-dihydro-furan-2-one 
• 670223-05-9 (S)-2-cyclohexylsulfanyl-N,N-dimethylpent-4-enamide 

Relevant academic research and scientific papers

Studies directed towards the enantioselective synthesis of ethisolide and isoavenaciolide

An asymmetric synthesis of an analog of ethisolide has been achieved by using as key steps two σ[3,3]rearrangements stereocontrolled by a sulfinyl group. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.

Asymmetric Induction of the Iodolactonization Reaction of α-Sulfurated γ-Unsaturated Amides

The 1,3-asymmetric iodolactonization reaction of enantiopure α-sulfurated γ-unsaturated amides has been investigated. With sulfinyl and sulfonyl groups, a poorly stereoselective reaction was observed, whereas with a sulfanyl moiety, the diastereoselectivi

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.