具有环丙基的α-亚氨基硫酯的极性反转反应。
An umpolung reaction of α-iminothioesters possessing a cyclopropyl group.
作者信息
Shimizu Makoto, Morimoto Takayoshi, Yanagi Yusuke, Mizota Isao, Zhu Yusong
机构信息
School of Energy Science and Engineering, Nanjing Tech University Nanjing 211816 Jiangsu Province China.
Department of Chemistry for Materials, Graduate School of Engineering, Mie University Tsu Mie 514-8507 Japan
出版信息
RSC Adv. 2020 Mar 10;10(17):9955-9963. doi: 10.1039/d0ra01152e. eCollection 2020 Mar 6.
An umpolung -alkylation reaction of α-cyclopropyl α-iminothioesters with diethylaluminum chloride or ethylmagnesium bromide affords the corresponding -ethylated α-aminothioesters in good yields. Subsequent oxidation and reaction of the -ethylated product with a thiolate or a chloride anion proceed effectively to give the ring-opened products in good yields. In contrast, relatively "hard" nucleophiles did not give the ring-opened products but gave the addition products to the iminium carbon.
α-环丙基α-亚氨基硫酯与二乙基氯化铝或乙基溴化镁发生极性反转烷基化反应，能以良好的产率得到相应的α-乙基化α-氨基硫酯。随后，α-乙基化产物进行氧化，并与硫醇盐或氯离子反应，能有效地以良好的产率得到开环产物。相比之下，相对“硬”的亲核试剂不能得到开环产物，而是得到亚胺鎓碳的加成产物。
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