Journal
ORGANIC LETTERS
Volume 16, Issue 5, Pages 1490-1493Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol500267w
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Funding
- Natural Science and Engineering Research Council of Canada (NSERC)
- Canada Research Chair Program
- FRQNT Centre in Green Chemistry, and Catalysis
- Universite de Montreal
- NSERC
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The Simmons-Smith reaction of zinc carbenoids with alkenes is a powerful method to access cyclopropanes containing various substitution patterns. This work exploits the high reactivity of aryldiazomethanes toward zinc halides to generate aryl-substituted carbenoids catalytically. These carbenoids are able to cyclopropanate various alkenes diastereoselectively, including unfunctionalized substrates such as styrenes. The zinc catalyst can be modified to tolerate the use of free allylic alcohols.
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