Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 45, Pages 20235-20241Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202009340
Keywords
[1; 1; 1]propellane; allylic zinc halides; strained molecules; zinc enolates
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Funding
- DFG
- LMU Munich
- Projekt DEAL
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We report a range of highly regioselective openings of [1.1.1]propellane with various allylic zinc halides, as well as zinc enolates of ketones, esters and nitriles. The resulting zincated bicyclopentanes (BCPs) were trapped with a range of electrophiles including acyl chlorides, sulfonothioates, hydroxylamino benzoates, tosyl cyanide as well as aryl and allyl halides, generating highly functionalized BCP-derivatives. The unusually high regioselectivity of these reactions has been rationalized using DFT calculations. A bioisostere of the synthetic opioid pethidine was prepared in 95 % yield in one step using this method.
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