Ring‐Opening Regio‐, Diastereo‐, and Enantioselective 1,3‐Chlorochalcogenation of Cyclopropyl Carbaldehydes

meso‐Cyclopropyl carbaldehydes are treated in the presence of an organocatalyst with sulfenyl and selenyl chlorides to afford 1,3‐chlorochalcogenated products. The transformation is achieved by a merged iminium–enamine activation. The enantioselective desymmetrization reaction, leading to three adja...

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Detalles Bibliográficos
Autores principales: Wallbaum, Jan, Garve, Lennart K. B., Jones, Peter G., Werz, Daniel B.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2016
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6680189/
https://www.ncbi.nlm.nih.gov/pubmed/27868248
http://dx.doi.org/10.1002/chem.201605265
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author Wallbaum, Jan
Garve, Lennart K. B.
Jones, Peter G.
Werz, Daniel B.
author_facet Wallbaum, Jan
Garve, Lennart K. B.
Jones, Peter G.
Werz, Daniel B.
author_sort Wallbaum, Jan
collection PubMed
description meso‐Cyclopropyl carbaldehydes are treated in the presence of an organocatalyst with sulfenyl and selenyl chlorides to afford 1,3‐chlorochalcogenated products. The transformation is achieved by a merged iminium–enamine activation. The enantioselective desymmetrization reaction, leading to three adjacent stereocenters, furnished the target products in complete regioselectivity and moderate to high diastereo‐ and enantioselectivities (d.r. up to 15:1 and e.r. up to 93:7).
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spelling pubmed-66801892019-08-09 Ring‐Opening Regio‐, Diastereo‐, and Enantioselective 1,3‐Chlorochalcogenation of Cyclopropyl Carbaldehydes Wallbaum, Jan Garve, Lennart K. B. Jones, Peter G. Werz, Daniel B. Chemistry Communications meso‐Cyclopropyl carbaldehydes are treated in the presence of an organocatalyst with sulfenyl and selenyl chlorides to afford 1,3‐chlorochalcogenated products. The transformation is achieved by a merged iminium–enamine activation. The enantioselective desymmetrization reaction, leading to three adjacent stereocenters, furnished the target products in complete regioselectivity and moderate to high diastereo‐ and enantioselectivities (d.r. up to 15:1 and e.r. up to 93:7). John Wiley and Sons Inc. 2016-11-29 2016-12-23 /pmc/articles/PMC6680189/ /pubmed/27868248 http://dx.doi.org/10.1002/chem.201605265 Text en © 2016 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Communications
Wallbaum, Jan
Garve, Lennart K. B.
Jones, Peter G.
Werz, Daniel B.
Ring‐Opening Regio‐, Diastereo‐, and Enantioselective 1,3‐Chlorochalcogenation of Cyclopropyl Carbaldehydes
title Ring‐Opening Regio‐, Diastereo‐, and Enantioselective 1,3‐Chlorochalcogenation of Cyclopropyl Carbaldehydes
title_full Ring‐Opening Regio‐, Diastereo‐, and Enantioselective 1,3‐Chlorochalcogenation of Cyclopropyl Carbaldehydes
title_fullStr Ring‐Opening Regio‐, Diastereo‐, and Enantioselective 1,3‐Chlorochalcogenation of Cyclopropyl Carbaldehydes
title_full_unstemmed Ring‐Opening Regio‐, Diastereo‐, and Enantioselective 1,3‐Chlorochalcogenation of Cyclopropyl Carbaldehydes
title_short Ring‐Opening Regio‐, Diastereo‐, and Enantioselective 1,3‐Chlorochalcogenation of Cyclopropyl Carbaldehydes
title_sort ring‐opening regio‐, diastereo‐, and enantioselective 1,3‐chlorochalcogenation of cyclopropyl carbaldehydes
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6680189/
https://www.ncbi.nlm.nih.gov/pubmed/27868248
http://dx.doi.org/10.1002/chem.201605265
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AT jonespeterg ringopeningregiodiastereoandenantioselective13chlorochalcogenationofcyclopropylcarbaldehydes
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