Ruthenium-Catalyzed Oxidative Formal Aza-Diels-Alder Reaction: Enantioselective Synthesis of Benzo[a]quinolizine-2-ones
Ruthenium-Catalyzed Oxidative Formal Aza-Diels-Alder Reaction: Enantioselective Synthesis of Benzo[a]quinolizine-2-ones
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钌催化氧化缩甲醛氮杂狄尔斯-阿尔德反应：苯并[a]喹嗪-2-酮的对映选择性合成
DOI：
10.1002/adsc.201700738
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发表时间：
2017
影响因子：
5.4
通讯作者：
Kantchev Eric Assen B
中科院分区：
文献类型：
--
作者：
Yao Yuan;Zhu Hai Jie;Li Fang;Zhu Cheng Feng;Luo Yun Fei;Wu Xiang;Kantchev Eric Assen B
介绍了1，2，3，4-四氢异喹啉与α，β-不饱和酮一锅氧化法合成热力学性质的(4R，11bS)-苯并[a]喹啉-2-酮衍生物的方法，该反应具有良好的对映体和非对映选择性。反应通过以叔丁基氢过氧化氢(TBHP)为氧化剂的Ru催化胺脱氢和手性硫脲催化的氮杂-[4+2]环加成反应进行，为合成这些有价值的杂环产品提供了一种步骤经济的策略。
A method for the preparation of thermodynamic (4R,11bS)‐benzo[a]quinolizine‐2‐one derivatives in good enantio‐ and diastereoselectivity by a one‐pot oxidative formal aza‐Diels–Alder reaction of 1,2,3,4‐tetrahydroisoquinolines and α,β‐unsaturated ketones is described. The reaction proceeds via tandem ruthenium‐catalyzed amine dehydrogenation usingtert‐butyl hydroperoxide (TBHP) as the oxidant and a chiral thiourea‐catalyzed formal aza‐[4+2] cycloaddition, providing a step‐economical strategy for the synthesis of these valuable heterocyclic products.