Chain Walking of Allylrhodium Species Towards Esters During Rhodium‐Catalyzed Nucleophilic Allylations of Imines

Allylrhodium species derived from δ‐trifluoroboryl β,γ‐unsaturated esters undergo chain walking towards the ester moiety. The resulting allylrhodium species react with imines to give products containing two new stereocenters and a Z‐alkene. By using a chiral diene ligand, products can be obtained wi...

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Autores principales: Martínez, Jose I., Smith, Joshua J., Hepburn, Hamish B., Lam, Hon Wai
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2015
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4736453/
https://www.ncbi.nlm.nih.gov/pubmed/26756445
http://dx.doi.org/10.1002/anie.201508964
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author Martínez, Jose I.
Smith, Joshua J.
Hepburn, Hamish B.
Lam, Hon Wai
author_facet Martínez, Jose I.
Smith, Joshua J.
Hepburn, Hamish B.
Lam, Hon Wai
author_sort Martínez, Jose I.
collection PubMed
description Allylrhodium species derived from δ‐trifluoroboryl β,γ‐unsaturated esters undergo chain walking towards the ester moiety. The resulting allylrhodium species react with imines to give products containing two new stereocenters and a Z‐alkene. By using a chiral diene ligand, products can be obtained with high enantioselectivities, where a pronounced matched/mismatched effect with the chirality of the allyltrifluoroborate is evident.
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spelling pubmed-47364532016-02-12 Chain Walking of Allylrhodium Species Towards Esters During Rhodium‐Catalyzed Nucleophilic Allylations of Imines Martínez, Jose I. Smith, Joshua J. Hepburn, Hamish B. Lam, Hon Wai Angew Chem Int Ed Engl Communications Allylrhodium species derived from δ‐trifluoroboryl β,γ‐unsaturated esters undergo chain walking towards the ester moiety. The resulting allylrhodium species react with imines to give products containing two new stereocenters and a Z‐alkene. By using a chiral diene ligand, products can be obtained with high enantioselectivities, where a pronounced matched/mismatched effect with the chirality of the allyltrifluoroborate is evident. John Wiley and Sons Inc. 2015-12-03 2016-01 /pmc/articles/PMC4736453/ /pubmed/26756445 http://dx.doi.org/10.1002/anie.201508964 Text en © 2015 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution (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
Martínez, Jose I.
Smith, Joshua J.
Hepburn, Hamish B.
Lam, Hon Wai
Chain Walking of Allylrhodium Species Towards Esters During Rhodium‐Catalyzed Nucleophilic Allylations of Imines
title Chain Walking of Allylrhodium Species Towards Esters During Rhodium‐Catalyzed Nucleophilic Allylations of Imines
title_full Chain Walking of Allylrhodium Species Towards Esters During Rhodium‐Catalyzed Nucleophilic Allylations of Imines
title_fullStr Chain Walking of Allylrhodium Species Towards Esters During Rhodium‐Catalyzed Nucleophilic Allylations of Imines
title_full_unstemmed Chain Walking of Allylrhodium Species Towards Esters During Rhodium‐Catalyzed Nucleophilic Allylations of Imines
title_short Chain Walking of Allylrhodium Species Towards Esters During Rhodium‐Catalyzed Nucleophilic Allylations of Imines
title_sort chain walking of allylrhodium species towards esters during rhodium‐catalyzed nucleophilic allylations of imines
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4736453/
https://www.ncbi.nlm.nih.gov/pubmed/26756445
http://dx.doi.org/10.1002/anie.201508964
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