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Highly Diastereoselective Synthesis of Methylenecyclobutanes by Merging Boron‐Homologation and Boron‐Allylation Strategies
Authors:Michael Eisold  Dr Dorian Didier
Institution:Department of Chemistry and Pharmacy, Ludwig‐Maximilians‐University Munich, Butenandtstrasse 5–13, 81377 Munich (Germany)
Abstract:A highly diastereoselective synthesis of methylenecyclobutanes possessing a quaternary stereocenter is reported, in which boron homologation of an easily‐generated cyclobutenylmetal species is performed, followed by an allylation reaction. Combining three steps in a one‐pot process further optimized the method, which afforded the expected adducts in excellent yields and stereoselectivity, starting from commercially available 4‐bromobutyne.
Keywords:allylboration  boron homologation  diastereoselectivity  methylenecyclobutanes  one‐pot reactions
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