Open AccessStereoselective Synthesis of Cyclobutanes by Contraction of Pyrrolidines
Author(s) -
Chunngai Hui,
Lukas Brieger,
Carsten Strohmann,
Andrey P. Antonchick
Publication year - 2021
Publication title -
journal of the american chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 7.115
H-Index - 612
eISSN - 1520-5126
pISSN - 0002-7863
DOI - 10.1021/jacs.1c10175
Subject(s) - cyclobutanes , chemistry , stereospecificity , stereocenter , stereoselectivity , natural product , stereochemistry , organic chemistry , combinatorial chemistry , enantioselective synthesis , cycloaddition , catalysis
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.