Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati 781039, Assam, India.
Org Lett. 2021 Apr 2;23(7):2437-2442. doi: 10.1021/acs.orglett.1c00302. Epub 2021 Mar 12.
A boronic acid catalyzed one-pot tandem reduction of quinolines to tetrahydroquinolines followed by reductive alkylation by the aldehyde has been demonstrated. This step-economcial synthesis of -alkyl tetrahydroquinolines has been achieved directly from readily available quinolines, aldehydes, and Hantzsch ester under mild reaction conditions. The mechanistic study demonstrates the unique behavior of organoboron catalysts as both Lewis acids and hydrogen-bond donors.
硼酸催化的喹啉一锅串联还原为四氢喹啉，然后通过醛的还原烷基化反应已经得到了证明。这种 - 烷基四氢喹啉的一步经济性合成方法直接从易得的喹啉、醛和 Hantzsch 酯在温和的反应条件下实现。该机理研究表明了有机硼催化剂作为路易斯酸和氢键供体的独特行为。
