Stereoselective Synthesis of Cyclobutanes by Contraction of Pyrrolidines

[Image: see text] 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 path...

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Autores principales: Hui, Chunngai, Brieger, Lukas, Strohmann, Carsten, Antonchick, Andrey P.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8603356/
https://www.ncbi.nlm.nih.gov/pubmed/34748319
http://dx.doi.org/10.1021/jacs.1c10175
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author Hui, Chunngai
Brieger, Lukas
Strohmann, Carsten
Antonchick, Andrey P.
author_facet Hui, Chunngai
Brieger, Lukas
Strohmann, Carsten
Antonchick, Andrey P.
author_sort Hui, Chunngai
collection PubMed
description [Image: see text] 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.
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spelling pubmed-86033562021-11-22 Stereoselective Synthesis of Cyclobutanes by Contraction of Pyrrolidines Hui, Chunngai Brieger, Lukas Strohmann, Carsten Antonchick, Andrey P. J Am Chem Soc [Image: see text] 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. American Chemical Society 2021-11-08 2021-11-17 /pmc/articles/PMC8603356/ /pubmed/34748319 http://dx.doi.org/10.1021/jacs.1c10175 Text en © 2021 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Hui, Chunngai
Brieger, Lukas
Strohmann, Carsten
Antonchick, Andrey P.
Stereoselective Synthesis of Cyclobutanes by Contraction of Pyrrolidines
title Stereoselective Synthesis of Cyclobutanes by Contraction of Pyrrolidines
title_full Stereoselective Synthesis of Cyclobutanes by Contraction of Pyrrolidines
title_fullStr Stereoselective Synthesis of Cyclobutanes by Contraction of Pyrrolidines
title_full_unstemmed Stereoselective Synthesis of Cyclobutanes by Contraction of Pyrrolidines
title_short Stereoselective Synthesis of Cyclobutanes by Contraction of Pyrrolidines
title_sort stereoselective synthesis of cyclobutanes by contraction of pyrrolidines
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8603356/
https://www.ncbi.nlm.nih.gov/pubmed/34748319
http://dx.doi.org/10.1021/jacs.1c10175
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AT strohmanncarsten stereoselectivesynthesisofcyclobutanesbycontractionofpyrrolidines
AT antonchickandreyp stereoselectivesynthesisofcyclobutanesbycontractionofpyrrolidines

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