Organocatalytic Enantioselective Allylic Etherification of Morita-Baylis-Hillman Carbonates and Silanols
Organocatalytic Enantioselective Allylic Etherification of Morita-Baylis-Hillman Carbonates and Silanols
复制标题
Morita-Baylis-Hillman 碳酸酯和硅烷醇的有机催化对映选择性烯丙基醚化
DOI：
10.1021/acs.joc.6b01931
复制
发表时间：
2016-10-21
影响因子：
3.6
通讯作者：
Guo, Hai-Ming
中科院分区：
文献类型：
--
作者：
Liu, Hui-Li;Xie, Ming-Sheng;Guo, Hai-Ming
首次报道了有机催化的Morita-Baylis-Hillman碳酸酯与硅醇的不对称烯丙基醚化反应。以改性金鸡纳生物碱（DHQD）（2）PYR为催化剂，合成了一系列芳香族、杂环族或脂肪族Morita-Baylis-Hillman碳酸酯（25例），与三苯基硅醇反应，得到了中等至良好的产率（高达98%）、高的区域选择性（>20：1）和良好的对映选择性（高达92%）。以二甲基苯基硅醇为亲核试剂，产率为60%，ee为87%。
The organocatalytic asymmetric allylic etherification reaction of Morita-Baylis-Hillman carbonates and silanols was reported for the first time. With modified cinchona alkaloid (DHQD)(2)PYR as the catalyst, a series of aromatic, heterocyclic, or aliphatic Morita-Baylis-Hillman carbonates (25 examples) worked well with triphenylsilanol, affording the corresponding products in moderate to good yields (up to 98%), high regioselectivities (>20:1), and good enantioselectivities (up to 92%). When dimethylphenylsilanol was used as the nucleophile, the product was obtained in 60% yield and 87% ee.