Wu Yikang, Huang Jia-Hui, Shen Xin, Hu Qi, Tang Chao-Jun, Li Liang
State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China.
Org Lett. 2002 Jun 27;4(13):2141-4. doi: 10.1021/ol025946n.
[reaction: see text] In DMSO cleavage of triethylsilyl (TES) ethers by o-iodoxybenzoic acid (IBX) was significantly faster than cleavage of tert-butyldimethylsilyl (TBS) ethers or further oxidation into carbonyl compounds. In most cases, TES protecting groups could be removed in good to excellent yields within 1 h, whereas similar TBS protecting groups remained intact under the same conditions. The procedure also could be adapted for direct one-pot conversion of TES ethers into carbonyl compounds.
[反应：见正文] 在二甲基亚砜（DMSO）中，邻碘氧基苯甲酸（IBX）对三乙基硅基（TES）醚的裂解速度明显快于叔丁基二甲基硅基（TBS）醚的裂解速度，也快于其进一步氧化为羰基化合物的速度。在大多数情况下，TES保护基可在1小时内以良好至优异的产率被除去，而类似的TBS保护基在相同条件下保持完整。该方法也可适用于将TES醚直接一锅转化为羰基化合物。
