Stereoselective Synthesis of Cyclobutanes by Contraction of Pyrrolidines

Chunngai Hui; Lukas Brieger; Carsten Strohmann; Andrey P Antonchick

doi:10.1021/jacs.1c10175

Stereoselective Synthesis of Cyclobutanes by Contraction of Pyrrolidines

J Am Chem Soc. 2021 Nov 17;143(45):18864-18870. doi: 10.1021/jacs.1c10175. Epub 2021 Nov 8.

Authors

Chunngai Hui^{1

2}, Lukas Brieger², Carsten Strohmann², Andrey P Antonchick^{1

2

3}

Affiliations

¹ Max Planck Institute of Molecular Physiology, Department of Chemical Biology, Otto-Hahn-Strasse 11, 44227 Dortmund, Germany.
² Technical University Dortmund, Faculty of Chemistry and Chemical Biology, Otto-Hahn-Strasse 6, 44221 Dortmund, Germany.
³ Nottingham Trent University, School of Science and Technology, Department of Chemistry and Forensics, Clifton Lane, NG11 8NS Nottingham, United Kingdom.

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.

Publication types

Research Support, Non-U.S. Gov't