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.
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Eisold et al. (2015) studied this question.
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