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Au-catalyzed synthesis of 5,6-dihydro-8H-indolizin-7-ones from N-(pent-2-en-4-ynyl)-beta-lactams.
Organic Letters ( IF 4.9 ) Pub Date : 2008 Nov 20 , DOI: 10.1021/ol802159v
Yu Peng 1 , Meng Yu 1 , Liming Zhang 1
Affiliation  

Au-catalyzed synthesis of 5,6-dihydro-8H-indolizin-7-ones from readily available N-(pent-2-en-4-ynyl)-beta-lactams is developed. In this reaction, a 5-exo-dig cyclization of the beta-lactam nitrogen to the Au-activated C-C triple bond is followed by heterolytic fragmentation of the amide bond, forming a highly nucleophilic acyl cation. An expedient formal synthesis of indolizidine 167B was easily achieved using this new method.

中文翻译:

Au催化从N-(戊-2-烯-4-炔基)-β-内酰胺合成5,6-二氢-8H-吲哚嗪-7-酮。

从容易获得的N-(戊-2-烯-4-炔基)-β-内酰胺的Au催化合成5,6-二氢-8H-吲哚嗪-7-酮。在该反应中,将β-内酰胺氮5-Au-dig环化为Au活化的CC三键,然后酰胺键进行杂合裂解,形成高度亲核的酰基阳离子。使用这种新方法很容易实现吲哚并立定167B的简便形式合成。
更新日期:2017-01-31
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