Synlett 2020; 31(01): 45-50
DOI: 10.1055/s-0039-1690196
cluster – 9th Pacific Symposium on Radical Chemistry
© Georg Thieme Verlag Stuttgart · New York

Samarium Diiodide Catalyzed Radical Cascade Cyclizations that Construct Quaternary Stereocenters

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Subject Editor: David Nicewicz and Corey StephensonSupport for this work was provided by the UK Engineering and Physical Sciences Research Council [EPSRC; EP/M005062/01 (Postdoctoral Fellowship to H.-M.H. and EPSRC Established Career Fellowship to D.J.P.)] and the EPSRC UK National EPR Facility and Service at the University of Manchester (NS/A000055/1).
Further Information

Publication History

Received: 25 July 2019

Accepted after revision: 15 August 2019

Publication Date:
28 August 2019 (online)


Published as part of the Cluster 9th Pacific Symposium on Radical Chemistry

Abstract

SmI2-catalyzed radical cascade cyclizations were used to generate complex carbocyclic products bearing quaternary stereocenters with high selectivity. Bicyclic scaffolds containing four contiguous stereocenters and one quaternary stereocenter were obtained in excellent yields (up to 99%) and with high diastereocontrol by using 5 mol% of SmI2 at ambient temperature in the absence of co-reductants or additives. Mechanistic studies support a radical relay mechanism.

Supporting Information

 
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