Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 47, Pages 14108-14112Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201506083
Keywords
cyclopropanes; carbenoids; NMR spectroscopy; reaction mechanisms; zinc
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Funding
- Natural Science and Engineering Research Council of Canada (NSERC)
- Canada Foundation for Innovation
- Canada Research Chair Program
- FQRNT Centre in Green Chemistry and Catalysis
- Universite de Montreal
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A stereoselective bromocyclopropanation of allylic alcohols using dibromomethylzinc bromide is described. Spectroscopic studies to monitor the formation of transient intermediates not only led to the development of a more-atom-economical halocyclopropanation reaction, but also highlighted the unique role of ether additives in the process. The desired bromo-substituted cyclopropanes were isolated in high yields and excellent diastereo- as well as enantioselectivities using readily available reagents.
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