通过 Rh(II)催化的 N-磺酰基-1,2,3-三唑与富电子芳族亲核试剂的反环化反应合成 6-取代的哌啶-3-酮。
Synthesis of 6-Substituted Piperidin-3-ones via Rh(II)-Catalyzed Transannulation of N-Sulfonyl-1,2,3-triazoles with Electron-Rich Aromatic Nucleophiles.
机构信息
Jilin Province Key Laboratory of Organic Functional Molecular Design & Synthesis, Department of Chemistry, Northeast Normal University , Changchun 130024, China.
State Key Laboratory of Elemento-Organic Chemistry, Nankai University , Tianjin 300071, China.
出版信息
Org Lett. 2017 Jun 16;19(12):3087-3090. doi: 10.1021/acs.orglett.7b01180. Epub 2017 May 25.
A highly diastereoselective rhodium(II)-catalyzed transannulation of aldehyde-tethered N-sulfonyl triazoles with electron-rich aromatic nucleophiles is reported for the first time to afford functionalized 6-substituted piperidin-3-ones. The reaction has a broad substrate scope including both aliphatic and aromatic N-sulfonyl-1,2,3-triazoles together with various aromatic nucleophiles. The addition of a catalytic amount of Lewis acid has proven to be crucial for the yield improvement. By employing this methodology, hardly accessible piperidin-3-ones bearing quaternary carbons could be obtained.
首次报道了手性铑（II）催化的醛基连接的 N-磺酰基三唑与富电子芳核试剂的高非对映选择性的 transannulation 反应，可得到官能化的 6-取代的哌啶-3-酮。该反应具有广泛的底物范围，包括脂肪族和芳香族 N-磺酰基-1,2,3-三唑以及各种芳基亲核试剂。添加催化量的路易斯酸已被证明对提高产率至关重要。通过采用这种方法，可以获得难以获得的带有季碳原子的哌啶-3-酮。
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