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Iron-Catalyzed Intramolecular Perezone-Type [5 + 2] Cycloaddition: Access to Tricyclo[6.3.1.01,6]dodecane
Yongjiang Liu1, Xiao Wang1, Song Chen1
1Key Laboratory of Green Chemistry &Technology of Ministry of Education, College of Chemistry , Sichuan University , Chengdu 610064 , China.
Abstract:
An iron-catalyzed perezone-type [5 + 2] cycloaddition toward tricyclo[6.3.1.01,6]dodecane scaffolds is presented, furnishing cycloadducts with two new C-C bonds and three to four stereogenic centers generated with typically good yields and excellent diastereoselectivities. Two independent conditions, catalytic FeCl3/PhCO3 tBu (0.5 equiv/1 equiv) and stoichiometric FeCl3(2 equiv), have been respectively manifested to be applicable for various substrates. Mechanistically, the reaction may proceed via iron-mediated generation of a carbon cationic center, which triggers subsequent [5 + 2] cyclization. Derivation of the cycloadduct was conducted to testify the applicability of this method.
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In a box plot, the minimum and maximum data values represent the lower and upper whiskers in the graph, and the median is designated as the center of the box in the chart. The first quartile and third...

