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Catalytic Asymmetric Ring-Opening/Cyclopropanation of Cyclic Sulfur Ylides: Construction of Sulfur-Containing Spirocyclopropyloxindoles with Three Vicinal Stereocenters
journal contribution
posted on 2018-12-06, 14:50 authored by Hongjiang Mei, Guihua Pan, Xiying Zhang, Lili Lin, Xiaohua Liu, Xiaoming FengA highly efficient
asymmetric ring-opening/cyclopropanation reaction
of (E)-3-(oxyethylidene)-2-oxoindolines with 1-alkyl-3-oxotetrahydro-1H-thiophen-1-ium salts as cyclic sulfur ylides was realized
by using a chiral N,N′-dioxide/Mg(OTf)2 complex as catalyst. A range of sulfur-containing syn,anti spirocyclopropyloxindoles with
three contiguous stereocenters were obtained in excellent yields with
excellent dr and good ee values under mild reaction conditions. The
origin of stereoselectivity was discussed.
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originreaction conditionsCatalyticstereocentercyclic sulfur ylidesspirocyclopropyloxindoleoxyethylideneSulfur-Containing Spirocyclopropyloxindolesring-openingAsymmetric1- alkyl -3-oxotetrahydro HConstructiondioxidesulfur-containing syncatalyststereoselectivitychiral Nthiophen -1-ium saltsRing-OpeningyieldVicinal Stereocentersee valuesCyclic Sulfur Ylides
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