通过还原不对称去对称反应催化对映选择性合成 N-C 轴向手性美布丙诺及其衍生物。
Catalytic Enantioselective Synthesis of N-C Axially Chiral Mebroqualone and Its Derivatives through Reductive Asymmetric Desymmetrization.
机构信息
Department of Applied Chemistry, Shibaura Institute of Technology , 3-7-5 Toyosu, Kohto-ku, Tokyo 135-8548, Japan.
出版信息
Org Lett. 2016 Nov 4;18(21):5700-5703. doi: 10.1021/acs.orglett.6b02865. Epub 2016 Oct 26.
In the presence of (R)-DTBM-SEGPHOS-Pd(OAc) catalyst, treatment of various 3-(2,6-dibromophenyl)quinazolin-4-ones with NaBH gave optically active N-C axially chiral quinazolinone (mebroqualone) derivatives through reductive asymmetric desymmetrization (enantioselective monohydrodebromination) followed by kinetic resolution of the resulting monobromophenyl products (up to 99% ee). The enantioselectivity strongly depended on the substituent (R) at the C4'position, amount of NaBH, and reaction temperature.
在（R）-DTBM-SEGPHOS-Pd(OAc) 催化剂的存在下，用 NaBH 处理各种 3-(2,6-二溴苯基)喹唑啉-4-酮，通过还原不对称去对称（对映选择性单氢脱溴）和随后对生成的单溴苯基产物进行动力学拆分（高达 99%ee），得到光学活性 N-C 轴向手性喹唑啉酮（美布丙嗪）衍生物。对映选择性强烈依赖于 C4'位的取代基（R）、NaBH 的用量和反应温度。
Zotero 插件