Stereoselective Synthesis of Polysubstituted Spiropentanes

[Image: see text] A new approach to polysubstituted spiropentanes is developed through a regio- and diastereoselective carbometalation of sp(2)-disubstituted cyclopropenes. The control of selectivity originates from a combined syn-facial diastereoselective carbometalation with a regio-directed addit...

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Autores principales: Cohen, Yair, Toledano, Dor, Marek, Ilan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9501800/
https://www.ncbi.nlm.nih.gov/pubmed/36088586
http://dx.doi.org/10.1021/jacs.2c07370
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author Cohen, Yair
Toledano, Dor
Marek, Ilan
author_facet Cohen, Yair
Toledano, Dor
Marek, Ilan
author_sort Cohen, Yair
collection PubMed
description [Image: see text] A new approach to polysubstituted spiropentanes is developed through a regio- and diastereoselective carbometalation of sp(2)-disubstituted cyclopropenes. The control of selectivity originates from a combined syn-facial diastereoselective carbometalation with a regio-directed addition. The regio-controlling element subsequently serves as a leaving group in an intramolecular nucleophilic substitution. This method allows the preparation of various polysubstituted spiropentanes with up to five contiguous stereocenters.
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spelling pubmed-95018002022-09-24 Stereoselective Synthesis of Polysubstituted Spiropentanes Cohen, Yair Toledano, Dor Marek, Ilan J Am Chem Soc [Image: see text] A new approach to polysubstituted spiropentanes is developed through a regio- and diastereoselective carbometalation of sp(2)-disubstituted cyclopropenes. The control of selectivity originates from a combined syn-facial diastereoselective carbometalation with a regio-directed addition. The regio-controlling element subsequently serves as a leaving group in an intramolecular nucleophilic substitution. This method allows the preparation of various polysubstituted spiropentanes with up to five contiguous stereocenters. American Chemical Society 2022-09-11 2022-09-21 /pmc/articles/PMC9501800/ /pubmed/36088586 http://dx.doi.org/10.1021/jacs.2c07370 Text en © 2022 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 Cohen, Yair
Toledano, Dor
Marek, Ilan
Stereoselective Synthesis of Polysubstituted Spiropentanes
title Stereoselective Synthesis of Polysubstituted Spiropentanes
title_full Stereoselective Synthesis of Polysubstituted Spiropentanes
title_fullStr Stereoselective Synthesis of Polysubstituted Spiropentanes
title_full_unstemmed Stereoselective Synthesis of Polysubstituted Spiropentanes
title_short Stereoselective Synthesis of Polysubstituted Spiropentanes
title_sort stereoselective synthesis of polysubstituted spiropentanes
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9501800/
https://www.ncbi.nlm.nih.gov/pubmed/36088586
http://dx.doi.org/10.1021/jacs.2c07370
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