Synthesis of enantiopure 2-azabicyclo[3.3.1]nonanes by a radical ring closure

Add time:07/20/2019    Source:sciencedirect.com

The first synthesis of enantiomerically pure 2-azabicyclo[3.3.1]nonanes by an intramolecular radical reaction of the trichloroacetamido group bearing an (S)-N-1-phenylethyl substituent with the silyl enol ether moiety in compounds 7 is described. The procedure allows the two enantiomers of the 2-azabicyclo[3.3.1]nonane-3,6-dione, 3 and ent-3, to be prepared separately. β-Lactam 8 and normorphan 9 are also formed from 7 through an initial radical translocation process in the cyclization step.

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