Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 52, Pages 15884-15887Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201507444
Keywords
allylboration; boron homologation; diastereoselectivity; methylenecyclobutanes; one-pot reactions
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Funding
- Chemical Industry Fund (FCI Liebig-fellowship)
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A highly diastereoselective synthesis of methylene-cyclobutanes 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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