不对称烯丙位 C-H 氧化反应在色满合成中的应用。
Asymmetric Allylic C-H Oxidation for the Synthesis of Chromans.
机构信息
Hefei National Laboratory for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China , Hefei 230026, China.
Collaborative Innovation Center of Chemical Science and Engineering , Tianjin, China.
出版信息
J Am Chem Soc. 2015 Oct 14;137(40):12732-5. doi: 10.1021/jacs.5b08477. Epub 2015 Oct 1.
An enantioselective intramolecular allylic C-H oxidation to generate optically active chromans has been accomplished under the cooperative catalysis of a palladium complex of chiral phosphoramidite ligand and 2-fluorobenzoic acid. Mechanistic studies suggest that this reaction commences with a Pd-catalyzed allylic C-H activation event and then undergoes asymmetric allylic alkoxylation. The synthetic significance of the method has been embodied by concisely building up a key chiral intermediate to access (+)-diversonol.
在手性膦酰胺配体钯配合物和 2-氟苯甲酸的协同催化作用下，实现了对映选择性的分子内烯丙基 C-H 氧化，以生成光学活性的 chromans。机理研究表明，该反应首先发生 Pd 催化的烯丙基 C-H 活化事件，然后进行不对称烯丙基烷氧基化。该方法的合成意义在于简洁地构建关键的手性中间体，以获得(+)-diversonol。
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