Abstract
An efficient approach to the multigram synthesis of 3-azabicyclo[3.1.1]heptanes is described. The method relied on the intramolecular imide formation in the properly 1,3-functionalized cyclobutane derivative. In turn, the latter compound was obtained via the diastereoselective Strecker reaction of readily accessible 3-oxocyclobutanecarboxylate. The resulting synthetic intermediate – 1-amino-3-azabicyclo[3.1.1]heptane-2,4-dione – was used to synthe¬size several monoprotected bicyclic diamines valuable as building blocks for medicinal chemistry, as well as a series of bridged analogs of Thalidomide, a known anticancer drug and a component of proteolysis-targeting chimeras (PROTACs).
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Supporting Information containing experimental details, compound characterization data, and copies of NMR spectra.
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