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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
A highly diastereoselective one-pot Ugi/radical spirocyclization/aza-Michael addition sequence
Salman Khan1, Abhradeep Chatterjee1, Akshay M Nair1
1Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai-400076, India. chandra.volla@chem.iitb.ac.in.
Abstract:
We hereby report a highly diastereoselective synthesis of chalcogenated azaspirotricycles via a one-pot Ugi/spirocyclization/aza-Michael addition sequence. The reaction proceeds via a key visible light mediated spirocyclization step under mild, metal-free and energy efficient conditions. A variety of complex sulfenylated and selenylated azaspirotricycles were obtained in good yields. The reaction was found to be scalable and preliminary mechanistic studies indicated that the spirocyclization step proceeds via radical intermediates.
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