Isoprene functionalization

Study on the α‐sulfenylation of 3‐sulfolenes

“…This result is consistent with an early report that the anionic cycloreversion of 3-sulfolene at room temperature produces the corresponding 2-1,3-butadienesulfinate stereoselectively [8].…”

The Use of Sulfonyl 1,3-Dienes in Organic Synthesis

“…Following this synthetic route, copper-catalyzed 1,4-addition of arenesulfonyl chlorides to acyclic and cyclic conjugated dienes has been applied to the preparation of 1-sulfonyl-substituted 1,3-dienes. , The 1-sulfonyl-4-chloro-2-alkenes obtained can be dehydrohalogenated in the presence of triethylamine to the corresponding acyclic or cyclic 1-sulfonyl 1,3-dienes, as is shown in Scheme for the synthesis of 1-(phenylsulfonyl)-1,3-cyclohexadiene ( 17 ). In the case of acyclic dienes such as isoprene E/Z mixtures are usually obtained 7 …”

“…In the case of acyclic dienes such as isoprene E/Z mixtures are usually obtained. 17 The iodosulfonylation reaction of conjugated dienes has been studied using in situ generated p-tolylsulfonyl iodide from sodium or mercury(II) p-toluenesulfinate and iodine. The δ-iodoalkenyl sulfones 19 obtained from the 1,4-addition process, undergo triethylamine-induced dehydrohalogenation to afford dienyl sulfones 20 (Scheme 8).…”

Enantioselective Sulfonation of Enones with Sulfonyl Imines by Cooperative N‐Heterocyclic‐Carbene/Thiourea/Tertiary‐Amine Multicatalysis

“…For example, with the thiourea cocatalyst These results suggested that the nucleophilic sulfinic anion was not delivered to enones as an isolated species. Chalcone-type enones with different aromatic substituents reacted smoothly to afford the corresponding g-ketosulfones in good yields with excellent enantioselectivity ( Table 2, entries [1][2][3][4][5][6][7][8][9][10][11][12][13][14]. We next examined the scope of the reaction under the optimized conditions (Table 2).…”