Nature Communications ( IF 14.7 ) Pub Date : 2022-12-07 , DOI: 10.1038/s41467-022-34916-z Takahiro Terunuma 1 , Yujiro Hayashi 1
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In this work, the enantioselective total synthesis of (–)-quinine has been accomplished in a pot-economical manner using five reaction vessels. In the first pot, reactions involve the diphenylprolinol silyl ether-mediated Michael reaction, aza-Henry reaction, hemiaminalization, and elimination of HNO2 (five reactions), affording a chiral tetrahydropyridine with excellent enantioselectivity. In the second pot, five reactions proceed with excellent diastereoselectivity to afford a trisubstituted piperidine with the desired stereochemistry. A further five reactions are carried out in the last one-pot sequence.
中文翻译：
有机催化剂介导的(–)-奎宁五锅法合成
在这项工作中，使用五个反应容器以罐式经济的方式完成了 (–)-奎宁的对映选择性全合成。在第一锅中，反应涉及二苯基脯氨醇甲硅烷基醚介导的迈克尔反应、氮杂亨利反应、半胺化和HNO 2消除（五个反应），得到具有优异对映选择性的手性四氢吡啶。在第二个罐中，五个反应以优异的非对映选择性进行，得到具有所需立体化学的三取代哌啶。在最后一锅顺序中进行另外五个反应。
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