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Synthesis of Substituted 1‐Alkylidenephthalanes via Lithium‐Promoted 5‐exo‐dig Cyclization
European Journal of Organic Chemistry ( IF 2.8 ) Pub Date : 2018-04-19 , DOI: 10.1002/ejoc.201800205
Paul Bunse 1 , Ernst-Ulrich Würthwein 2 , Bernhard Wünsch 1, 3
Affiliation  

The 1‐alkylidenephthalane scaffold is found in several biological active compounds. In order to synthesize 1‐alkylidenephthalanes, a Domino reaction was developed using 2‐alkynyl‐substituted bromobenzenes. Successive bromine/lithium exchange, nucleophilic addition at aldehydes or ketone 5‐exo‐dig cyclization and hydrolysis resulted in aldehydes or esters in high yield. The 5‐exo‐dig cyclization key step was theoretically analyzed by DFT calculations.
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中文翻译:

锂促进的5-exo-dig环化反应合成取代的1-炔基萘

在一些生物活性化合物中发现了1-亚烷基萘骨架。为了合成1-亚烷基萘,使用2-炔基取代的溴苯开发了多米诺反应。连续的溴/锂交换,在醛基上的亲核加成或酮的5 exo-dig环化和水解导致醛或酯的高收率。通过DFT计算从理论上分析了5 exo-dig环化关键步骤。
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更新日期:2018-04-19
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