Stereoselective Synthesis of Cyclobutanes by Contraction of Pyrrolidines
Chunngai Hui, Lukas Brieger, Carsten Strohmann, Andrey P. Antonchick
Abstract
Here we report a contractive synthesis of multisubstituted cyclobutanes containing multiple stereocenters from readily accessible pyrrolidines using iodonitrene chemistry. Mediated by a nitrogen extrusion process, the stereospecific synthesis of cyclobutanes involves a radical pathway. Unprecedented unsymmetrical spirocyclobutanes were prepared successfully, and a concise, formal synthesis of the cytotoxic natural product piperarborenine B is reported.
Topics & Concepts
CyclobutanesChemistryStereospecificityStereocenterStereoselectivityNatural productStereochemistryCombinatorial chemistryOrganic chemistryEnantioselective synthesisCycloadditionCatalysisOxidative Organic Chemistry ReactionsSynthesis and Catalytic ReactionsCatalytic C–H Functionalization Methods