有机催化对映选择性烯丙基醚化 Morita-Baylis-Hillman 碳酸酯和硅醇。
Organocatalytic Enantioselective Allylic Etherification of Morita-Baylis-Hillman Carbonates and Silanols.
机构信息
Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, School of Chemistry and Chemical Engineering, Henan Normal University , Xinxiang, Henan 453007, China.
出版信息
J Org Chem. 2016 Oct 21;81(20):10035-10042. doi: 10.1021/acs.joc.6b01931. Epub 2016 Oct 3.
The organocatalytic asymmetric allylic etherification reaction of Morita-Baylis-Hillman carbonates and silanols was reported for the first time. With modified cinchona alkaloid (DHQD)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.
首次报道了手性有机催化的 Morita-Baylis-Hillman 碳酸酯与硅醇的不对称烯丙基醚化反应。以改性的金鸡纳碱(DHQD)PYR 作为催化剂，一系列芳香族、杂环或脂肪族的 Morita-Baylis-Hillman 碳酸酯（25 个实例）与三苯基硅醇反应良好，以中等至良好的收率（高达 98%）、高区域选择性（>20:1）和良好的对映选择性（高达 92%）得到相应产物。当使用二甲基苯基硅醇作为亲核试剂时，产物的收率为 60%，对映选择性为 87%ee。
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