Journal
ORGANIC LETTERS
Volume 21, Issue 17, Pages 6800-6804Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b02426
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Funding
- Natural Sciences and Engineering Research Council of Canada (NSERC)
- NSERC
- Walter C. Sumner Foundation
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Bicyclo[1.1.1]pentanes are effective bioisoteres for aromatic rings, tert-butyl groups, and alkynes. Here we report the first method to synthesize 3-alkylbicyclo[1.1.1]pentan-1-amines directly from [1.1.1]propellane via sequential addition of magnesium amides and alkyl electrophiles. The mild reaction conditions tolerate a variety of important functional groups and enable efficient incorporation of several pharmaceutically relevant amines onto the bicyclo[1.1.1]pentane scaffold. This method's utility is highlighted by its ability to significantly streamline the syntheses of several important bicyclo[1.1.1]pentan-1-amine building blocks.
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