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Benjamin M. Reeves Hamish B. Hepburn Alexandru Grozavu Peter J. Lindsay‐Scott Timothy J. Donohoe 《Angewandte Chemie (Weinheim an der Bergstrasse, Germany)》2019,131(44):15844-15848
A transition‐metal‐free reductive hydroxymethylation reaction has been developed, enabling the preparation of tetrahydroisoquinolines bearing C4‐quaternary centers from the corresponding isoquinolines. Deuterium labelling studies and control experiments enable a potential mechanism to be elucidated which features a key Cannizzaro‐type reduction followed by an Evans–Tishchenko reaction. When isoquinolines featuring a proton at the 4‐position are used, a tandem methylation‐hydroxymethylation occurs, leading to the formation of 2 new C?C bonds in one pot. 相似文献
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