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Phosphine-catalyzed [3 + 2] annulation reaction: highly regio- and diastereoselective synthesis of 2-azaspiro[4.4]nonene-1,3-diones
Organic & Biomolecular Chemistry ( IF 3.2 ) Pub Date : 2017-08-24 00:00:00 , DOI: 10.1039/c7ob01957b
Wenjun Luo 1, 2, 3, 4, 5 , Haiwen Hu 1, 2, 3, 4, 5 , Sanfei Nian 1, 2, 3, 4, 5 , Liang Qi 1, 2, 3, 4, 5 , Fei Ling 1, 2, 3, 4, 5 , Weihui Zhong 1, 2, 3, 4, 5
Affiliation  

A novel phosphine-catalyzed [3 + 2] annulation of γ-substituted allenoates with succinimides was developed, which was successfully applied to the synthesis of 2-azaspiro[4.4]nonene-1,3-dione derivatives. The reaction afforded the desired products in moderate to high yields (up to 96%) with excellent regioselectivities and diastereoselectivities (up to >99 : 1 dr). A plausible reaction mechanism has also been proposed based on previous literature.

中文翻译:

膦催化的[3 + 2]环化反应:2-氮杂螺[4.4]壬烯-1,3-二酮的高度区域选择性和非对映选择性合成

开发了一种新型的膦催化的琥珀酰亚胺与γ-取代的烯丙酸酯的[3 + 2]环化反应,将其成功地用于2-氮杂螺[4.4]壬烯-1,3-二酮衍生物的合成。反应,得到所需的产品在中到高的产率(高达96%)具有优异的区域选择性和非对映选择性(高达> 99   1个,DR)。基于先前的文献,也已经提出了合理的反应机理。
更新日期:2017-09-20
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