Decarboxylative Umpolung Synthesis of Amines from Carbonyl Compounds
Decarboxylative Umpolung Synthesis of Amines from Carbonyl Compounds
复制标题
羰基化合物脱羧还原合成胺
DOI：
10.1055/s-0040-1707157
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发表时间：
2020-10-01
期刊：
影响因子：
2
通讯作者：
Zhao, Baoguo
中科院分区：
文献类型：
--
作者：
Chen, Wen-Wen;Zhao, Baoguo
2-氮杂烯丙基阴离子是一类重要的中间体，在与各种亲电试剂的功能化反应中具有广泛的应用。由芳香醛和α，α-二苯基甘氨酸形成的亚胺的脱羧提供了一种有趣且有效的方式来产生离域的2-氮杂烯丙基阴离子，其对不同的亲电试剂显示出高反应性，在2-氮杂烯丙基阴离子的二苯基酮亚胺芳基碳处具有优异的区域选择性。该转化在非常温和的条件下以良好的产率产生各种胺。这篇Synpacts文章重点介绍了羰基化合物脱羧还原合成胺的最新进展。1引言2羰基化合物与不同亲电体的脱羧Umpolung反应2.1与π-烯丙基-Pd（II）物种的反应2.2与Morita-Baylis-Hillman加合物的反应2.3与亚胺的反应2.3.1与N-Ts亚胺的分子间反应2.3.2与手性N-叔丁基亚磺酰亚胺的分子内反应2.4与醛和酮的反应3 α，β-不饱和醛与醛\ 4结论
2-Azaallyl anions are valuable intermediates which have versatile applications in functionalization with various electrophiles. Decarboxylation of the imines formed from aromatic aldehydes and alpha,alpha-diphenylglycine provides an interesting and efficient way to generate delocalized 2-azaallyl anions, which display high reactivity toward different electrophiles with excellent regioselectivity at the diphenylketimino aryl carbon of the 2-azaallyl anions. The transformation produces various amines in good yields under very mild conditions. This Synpacts article highlights the recent advances on the decarboxylative umpolung synthesis of amines from carbonyl compounds. 1 Introduction2 Decarboxylative Umpolung Reactions of Carbonyl Compounds with Different Electrophiles2.1 Reaction with pi-Allyl-Pd(II) Species2.2 Reaction with Morita-Baylis-Hillman Adducts2.3 Reaction with Imines2.3.1 Intermolecular Reaction withN-Ts Imines2.3.2 Intramolecular Reaction with ChiralN-tert-Butanesulfinyl Imines2.4 Reaction with Aldehydes and Ketones3 Decarboxylative Umpolung Reaction of alpha,beta-Unsaturated Aldehydes with Aldehydes \ 4 Conclusion