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One‐Pot Generation of Bicyclo[3.1.0]hexanols and Cyclohexanones by Double Interrupted Nazarov Reactions
Chemistry - A European Journal ( IF 4.3 ) Pub Date : 2018-03-26 , DOI: 10.1002/chem.201800758
Shorena Gelozia 1 , Yonghoon Kwon 1 , Robert McDonald 1 , F. G. West 1
Affiliation  

Organoaluminum‐mediated double interrupted Nazarov cyclization to access bicyclo[3.1.0]hexanols via nucleophilic methyl attack followed by Simmons–Smith‐type electrophilic cyclopropanation is reported. These alcohols can undergo ring opening to afford cyclohexanones or cyclohexenones, broadening the range of scaffolds available via interrupted Nazarov reaction beyond the usual cyclopentanoid products. Throughout the sequence, a total of four new C−C bonds are formed, along with four new stereogenic centers.

中文翻译:

双中断Nazarov反应一锅法生成双环[3.1.0]己醇和环己酮

据报道,有机铝介导的双中断Nazarov环化反应通过亲核甲基攻击随后通过Simmons-Smith型亲电环丙烷化作用来进入双环[3.1.0]己醇。这些醇可以开环得到环己酮或环己酮,使通过中断的Nazarov反应可利用的支架的范围扩大到常规的环戊烷类产物之外。在整个序列中,总共形成了四个新的C-C键,以及四个新的立体生成中心。
更新日期:2018-03-26
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