Xiao Ben-Xian, Shi Chong-Hui, Liang Shu-Yuan, Jiang Bo, Du Wei, Chen Ying-Chun
Key Laboratory of Drug-Targeting and Drug Delivery System of the Ministry of Education and Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy , Sichuan University , Chengdu 610041 , China.
College of Pharmacy , Third Military Medical University , Shapingba, Chongqing 400038 , China.
Org Lett. 2019 Sep 20;21(18):7554-7557. doi: 10.1021/acs.orglett.9b02827. Epub 2019 Aug 30.
Under the catalysis of Lewis bases, cyclic enones bearing an α-(2-furyl) motif can undergo remote Friedel-Crafts reaction with electrophilic reagents via a HOMO-activation strategy, proceeding in a formal vinylogous Rauhut-Currier or Morita-Baylis-Hillman-type reaction pattern. Moreover, even less reactive α-(2-benzofuranyl)-substituted cyclopeten-2-ones can be similarly HOMO-raised and furnish [4 + 2] products with alkylidenemalononitriles in a cascade Friedel-Crafts/Michael addition process.
在路易斯碱的催化作用下，带有α-(2-呋喃基) motif的环状烯酮可通过HOMO活化策略与亲电试剂发生远程傅克反应，以形式上类似乙烯型劳乌特-柯里尔或森田-贝利斯-希尔曼型反应模式进行。此外，即使是活性较低的α-(2-苯并呋喃基)取代的环戊烯-2-酮也能以类似方式提高HOMO，并在级联傅克/迈克尔加成过程中与亚烷基丙二腈生成[4 + 2]产物。
