Catalytic Asymmetric Synthesis of Phosphoryl‐1,4‐dihydropyridazines via an Enantioselective Allylic Alkylation/1,3‐Dipolar Cycloaddition/Rearrangement Reaction Sequence
Catalytic Asymmetric Synthesis of Phosphoryl‐1,4‐dihydropyridazines via an Enantioselective Allylic Alkylation/1,3‐Dipolar Cycloaddition/Rearrangement Reaction Sequence
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DOI：
10.1002/adsc.201600353
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发表时间：
2016-07
影响因子：
5.4
通讯作者：
Fei Du;L. Yin;Yanqiang Ning;Yungui Peng
中科院分区：
文献类型：
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作者：
Fei Du;L. Yin;Yanqiang Ning;Yungui Peng
基于不对称烯丙基烷基化/分子内1,3-偶极环加成/重排反应序列，开发了一种合成手性磷酰基-1,4-二氢哒嗪衍生物的新方法，以高产率和高对映选择性获得了各种手性3-磷酰基-4-芳基-1,4-二氢哒嗪-5-羧酸酯。此外，通过还原 Morita-Baylis-Hillman 碳酸酯和 α-重氮膦酸酯的烯丙基烷基化产物，也可以轻松制备手性 4,5-二氢哒嗪酮衍生物。
A novel methodology has been developed for the synthesis of chiral phosphoryl-1,4-dihydropyridazine derivatives based on an asymmetric allylic alkylation/intramolecular 1,3-dipolar cycloaddition/rearrangement reaction sequence, various chiral 3-phosphoryl-4-aryl-1,4-dihydropyridazine-5-carboxylates were achieved in high yields with high enantioselectivities. Moreover, chiral 4,5-dihydropyridazinone derivatives were also facilely furnished by the reduction of the allylic alkylation products of Morita–Baylis–Hillman carbonates and α-diazophosphonates.