Enantioselective Assembly of Spirocyclic Oxindole-dihydropyranones through NHC-Catalyzed Cascade Reaction of Isatins with N-Hydroxybenzotriazole Esters of alpha,beta-Unsaturated Carboxylic Acid
Enantioselective Assembly of Spirocyclic Oxindole-dihydropyranones through NHC-Catalyzed Cascade Reaction of Isatins with N-Hydroxybenzotriazole Esters of alpha,beta-Unsaturated Carboxylic Acid
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NHC 催化靛红与 α,β-不饱和羧酸 N-羟基苯并三唑酯级联反应对映选择性组装螺环羟吲哚-二氢吡喃酮
DOI：
10.1021/jo502920w
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发表时间：
2015
影响因子：
3.6
通讯作者：
Yao Changsheng
中科院分区：
文献类型：
--
作者：
Que Yonglei;Li Tuanjie;Yu Chenxia;Wang Xiang-Shan;Yao Changsheng
以含手性四取代碳立体中心的α，β-不饱和羧酸的N-羟基苯并三氮唑酯为原料，在γ-H催化下合成了螺环氧吲哚-二氢吡喃酮类化合物。高的对映体选择性、原料的易得性、组装的简便性以及最终产物潜在的生物学意义使该方案成为合成螺环杂环的一个有吸引力的替代方案。
An NHC-catalyzed formal [4 + 2] reaction of isatins withN-hydroxybenzotriazole ester of α,β-unsaturated carboxylic acids bearing γ-H to construct spirocyclic oxindole-dihydropyranones featuring a chiral tetrasubstituted carbon stereogenic center was developed. The high enantioselectivity, the ready availability of the raw materials, the facile assembly, and the potential biological significance of the final products make this protocol an attractive alternative for the synthesis of spirocyclic heterocycles.