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Org Lett. 2019 Aug 13. doi: 10.1021/acs.orglett.9b02426. [Epub ahead of print]

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

Author information

1
Department of Chemistry , McGill University , 801 Sherbrooke West , Montreal , QC H3A 2K6 , Canada.
2
Inception Sciences , 6175 Nancy Ridge Drive , San Diego , California 92121 , United States.
3
Inception Sciences , 7150 Frederick-Banting Street , Saint-Laurent , QC H4S 2A1 , Canada.

Abstract

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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