苯基硫代二氟甲基硅烷对手性环状硝酮的立体选择性亲核加成：偕二氟亚甲基化多羟基吡咯里西啶和吲哚里西啶的不对称合成
Stereoselective nucleophilic addition of PhSCF2 SiMe3 to chiral cyclic nitrones: asymmetric synthesis of gem-difluoromethylenated polyhydroxypyrrolizidines and -indolizidines.
作者信息
Korvorapun Korkit, Soorukram Darunee, Kuhakarn Chutima, Tuchinda Patoomratana, Reutrakul Vichai, Pohmakotr Manat
机构信息
Center of Excellence for Innovation in Chemistry (PERCH-CIC) and Department of Chemistry, Faculty of Science, Mahidol University, Rama VI Road, Bangkok 10400 (Thailand).
出版信息
Chem Asian J. 2015 Apr;10(4):948-68. doi: 10.1002/asia.201403023. Epub 2014 Nov 21.
Fluoride-catalyzed nucleophilic addition of a difluoro(phenylsulfanyl)methyl group ("PhSCF2 ") generated from PhSCF2 SiMe3 to nitrones was accomplished in satisfactory yields. High diastereoselectivities were observed with chiral polyoxygenated cyclic nitrones to provide the corresponding adducts, which were further manipulated to afford gem-difluoromethylenated polyhydroxypyrrolizidines and -indolizidines.
由PhSCF₂SiMe₃生成的二氟（苯硫基）甲基基团（“PhSCF₂ ”）在氟化物催化下与硝酮发生亲核加成反应，产率令人满意。对手性多氧化环状硝酮观察到了高非对映选择性，得到相应的加合物，这些加合物进一步经处理得到偕二氟亚甲基化的多羟基吡咯里西啶和吲哚里西啶。
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