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A Boron Alkylidene–Alkene Cycloaddition Reaction: Application to the Synthesis of Aphanamal
Author(s) -
Liu Xun,
Deaton T. Maxwell,
Haeffner Fredrik,
Morken James P.
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201705720
Subject(s) - cycloaddition , alkene , boron , natural product , scope (computer science) , chemistry , combinatorial chemistry , aside , ring (chemistry) , organic chemistry , catalysis , computer science , philosophy , programming language , linguistics
We describe an unusual net [2+2] cycloaddition reaction between boron alkylidenes and unactivated alkenes. This reaction provides a new method for the construction of carbocyclic ring systems bearing versatile organoboronic esters. Aside from surveying the scope of this reaction, we provide details about the mechanistic underpinnings of this process, and examine its application to the synthesis of the natural product aphanamal.