Stereogenic boron in 2-amino-1,1-diphenylethanol-based boronate–imine and amine complexes

Racemic boronate–imine and boronate–amine complexes 8 and 10, both featuring a stereogenic boron atom were synthesized from 2-amino-1,1-diphenylethanol (5) and characterized by crystal structure analyses. Proof of enantiomerism at the boron center for the novel boronate–amine complex 10 was establis...

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Detalles Bibliográficos
Autores principales: Schlecht, Sebastian, Frank, Walter, Braun, Manfred
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2011
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3107563/
https://www.ncbi.nlm.nih.gov/pubmed/21647267
http://dx.doi.org/10.3762/bjoc.7.72
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author Schlecht, Sebastian
Frank, Walter
Braun, Manfred
author_facet Schlecht, Sebastian
Frank, Walter
Braun, Manfred
author_sort Schlecht, Sebastian
collection PubMed
description Racemic boronate–imine and boronate–amine complexes 8 and 10, both featuring a stereogenic boron atom were synthesized from 2-amino-1,1-diphenylethanol (5) and characterized by crystal structure analyses. Proof of enantiomerism at the boron center for the novel boronate–amine complex 10 was established by separation of the enantiomers. Racemization barriers were found to be in the same range for both amine and imine complexes (100–110 kJ/mol).
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spelling pubmed-31075632011-06-06 Stereogenic boron in 2-amino-1,1-diphenylethanol-based boronate–imine and amine complexes Schlecht, Sebastian Frank, Walter Braun, Manfred Beilstein J Org Chem Full Research Paper Racemic boronate–imine and boronate–amine complexes 8 and 10, both featuring a stereogenic boron atom were synthesized from 2-amino-1,1-diphenylethanol (5) and characterized by crystal structure analyses. Proof of enantiomerism at the boron center for the novel boronate–amine complex 10 was established by separation of the enantiomers. Racemization barriers were found to be in the same range for both amine and imine complexes (100–110 kJ/mol). Beilstein-Institut 2011-05-16 /pmc/articles/PMC3107563/ /pubmed/21647267 http://dx.doi.org/10.3762/bjoc.7.72 Text en Copyright © 2011, Schlecht et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Schlecht, Sebastian
Frank, Walter
Braun, Manfred
Stereogenic boron in 2-amino-1,1-diphenylethanol-based boronate–imine and amine complexes
title Stereogenic boron in 2-amino-1,1-diphenylethanol-based boronate–imine and amine complexes
title_full Stereogenic boron in 2-amino-1,1-diphenylethanol-based boronate–imine and amine complexes
title_fullStr Stereogenic boron in 2-amino-1,1-diphenylethanol-based boronate–imine and amine complexes
title_full_unstemmed Stereogenic boron in 2-amino-1,1-diphenylethanol-based boronate–imine and amine complexes
title_short Stereogenic boron in 2-amino-1,1-diphenylethanol-based boronate–imine and amine complexes
title_sort stereogenic boron in 2-amino-1,1-diphenylethanol-based boronate–imine and amine complexes
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3107563/
https://www.ncbi.nlm.nih.gov/pubmed/21647267
http://dx.doi.org/10.3762/bjoc.7.72
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