通过铑催化的不对称氢化反应实现手性 2-取代 2,3-二氢苯并[1,4]二恶烷衍生物的对映选择性获得。
Enantioselective Access to Chiral 2-Substituted 2,3-Dihydrobenzo[1,4]dioxane Derivatives through Rh-Catalyzed Asymmetric Hydrogenation.
机构信息
Key Laboratory of Biomedical Polymers, Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, College of Chemistry and Molecular Sciences , Wuhan University , Wuhan , Hubei 430072 , People's Republic of China.
Key Laboratory of Synthetic and Natural Functional Molecule, Chemistry of Ministry of Education, College of Chemistry and Materials Science , Northwest University , Xi'an , People's Republic of China.
出版信息
Org Lett. 2018 Jul 20;20(14):4173-4177. doi: 10.1021/acs.orglett.8b01469. Epub 2018 Jul 3.
Rh-catalyzed asymmetric hydrogenation of various benzo[ b][1,4]dioxine derivatives was successfully developed to prepare chiral 2-substituted 2,3-dihydrobenzo[1,4]dioxane derivatives using ZhaoPhos and N-methylation of ZhaoPhos ligands with high yields and excellent enantioselectivities (up to 99% yield, >99% enantiomeric excess (ee), turnover number (TON) = 24 000). Moreover, this asymmetric hydrogenation methodology, as the key step with up to 10 000 TON, was successfully applied to develop highly efficient synthetic routes for the construction of some important biologically active molecules, such as MKC-242, WB4101, BSF-190555, and ( R)-doxazosin·HCl.
成功开发了 Rh 催化的各种苯并[ b][1,4]二恶烷衍生物的不对称氢化反应，使用 ZhaoPhos 和 ZhaoPhos 配体的 N-甲基化，以高产率和优异的对映选择性（高达 99%的收率、>99%的对映体过量（ee）、转化数（TON）=24000）制备手性 2-取代 2,3-二氢苯并[1,4]二恶烷衍生物。此外，该不对称氢化方法学作为最高可达 10000TON 的关键步骤，成功应用于开发一些重要生物活性分子的高效合成途径，如 MKC-242、WB4101、BSF-190555 和（R）-多沙唑嗪·HCl。
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