Aminoalkylation of [1.1.1]Propellane Enables Direct Access to High-Value 3‑Alkylbicyclo[1.1.1]pentan-1-amines

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 re...

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Bibliographic Details
Published inOrganic letters Vol. 21; no. 17; pp. 6800 - 6804
Main Authors Hughes, Jonathan M. E, Scarlata, David A, Chen, Austin C.-Y, Burch, Jason D, Gleason, James L
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 06.09.2019
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
BIOLOGICAL EVALUATION
DESIGN
DERIVATIVES
BRIDGEHEAD
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Summary: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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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b02426