An efficient and selective method for the deprotection of primary alcoholic tert-butyl-dimethylsilyl (TBS) ethers using SnCl_2·2H_2O as catalyst is described. The reaction conditionsallow primary alcoholic TBS et...An efficient and selective method for the deprotection of primary alcoholic tert-butyl-dimethylsilyl (TBS) ethers using SnCl_2·2H_2O as catalyst is described. The reaction conditionsallow primary alcoholic TBS ethers to be desilylated chemoselectively in the presence of phenolicTBS ethers, secondary and tertiary alcolholic TBS ethers, and the extensively used TBDPS-,acetyl-, benzyloxycarbonyl-, p-toluenesulfonyl- and benzyl protective groups.展开更多
Copper was found to be able to promote the SnCl2-mediated carbonyl allylation reactions in water, giving the corresponding homoallylic alcohol products in very high yields. Detailed studies showed that the reaction co...Copper was found to be able to promote the SnCl2-mediated carbonyl allylation reactions in water, giving the corresponding homoallylic alcohol products in very high yields. Detailed studies showed that the reaction could be applied to a variety of carbonyl compounds including those with hydroxyl, amino and nitro groups. It was also found that this reaction showed good regioselectivities for some substrates. Furthermore, carefully controled ex-periments and in situ NMR measurements provided important insights into the mechanism of the newly developed reaction.展开更多
文摘An efficient and selective method for the deprotection of primary alcoholic tert-butyl-dimethylsilyl (TBS) ethers using SnCl_2·2H_2O as catalyst is described. The reaction conditionsallow primary alcoholic TBS ethers to be desilylated chemoselectively in the presence of phenolicTBS ethers, secondary and tertiary alcolholic TBS ethers, and the extensively used TBDPS-,acetyl-, benzyloxycarbonyl-, p-toluenesulfonyl- and benzyl protective groups.
基金Project supported by Chinese Academy of Sciences (No. KJCXZ-SW-04) and the National Natural Science Foundation of China (No. 20332020).
文摘Copper was found to be able to promote the SnCl2-mediated carbonyl allylation reactions in water, giving the corresponding homoallylic alcohol products in very high yields. Detailed studies showed that the reaction could be applied to a variety of carbonyl compounds including those with hydroxyl, amino and nitro groups. It was also found that this reaction showed good regioselectivities for some substrates. Furthermore, carefully controled ex-periments and in situ NMR measurements provided important insights into the mechanism of the newly developed reaction.
