(4R)-4-Benzyl-3-{(4S)-4-chloro-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]butano­yl}-1,3-oxazolidin-2-one

The title compound, C(19)H(24)ClNO(5), was synthesized and subsequently employed in an Evans alkyl­ation. The purpose was to prove the absolute configuration in the projected synthesis of the side chain of (–)-Lytophilippine A. The oxazolidinone and the isopropylidene acetal rings have twisted confo...

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Autores principales: Börding, Sandra, Strohmann, Carsten, Preut, Hans, Hiersemann, Martin
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2011
Materias:
Organic Papers
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3254509/
https://www.ncbi.nlm.nih.gov/pubmed/22259453
http://dx.doi.org/10.1107/S1600536811053840
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author Börding, Sandra
Strohmann, Carsten
Preut, Hans
Hiersemann, Martin
author_facet Börding, Sandra
Strohmann, Carsten
Preut, Hans
Hiersemann, Martin
author_sort Börding, Sandra
collection PubMed
description The title compound, C(19)H(24)ClNO(5), was synthesized and subsequently employed in an Evans alkyl­ation. The purpose was to prove the absolute configuration in the projected synthesis of the side chain of (–)-Lytophilippine A. The oxazolidinone and the isopropylidene acetal rings have twisted conformations. The oxazolidinone and side-chain carbonyl groups are orientated in an anti­periplanar arrangement to minimize van der Waals repulsions. Furthermore, the Cl atom and the acetonide-protected secondary alcohol are also in an anti­periplanar arrangement with a torsion angle of 173.64 (14)°. The absolute configuration was determined and agrees with the configuration of the used chiral auxiliary.
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spelling pubmed-32545092012-01-18 (4R)-4-Benzyl-3-{(4S)-4-chloro-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]butano­yl}-1,3-oxazolidin-2-one Börding, Sandra Strohmann, Carsten Preut, Hans Hiersemann, Martin Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(19)H(24)ClNO(5), was synthesized and subsequently employed in an Evans alkyl­ation. The purpose was to prove the absolute configuration in the projected synthesis of the side chain of (–)-Lytophilippine A. The oxazolidinone and the isopropylidene acetal rings have twisted conformations. The oxazolidinone and side-chain carbonyl groups are orientated in an anti­periplanar arrangement to minimize van der Waals repulsions. Furthermore, the Cl atom and the acetonide-protected secondary alcohol are also in an anti­periplanar arrangement with a torsion angle of 173.64 (14)°. The absolute configuration was determined and agrees with the configuration of the used chiral auxiliary. International Union of Crystallography 2011-12-17 /pmc/articles/PMC3254509/ /pubmed/22259453 http://dx.doi.org/10.1107/S1600536811053840 Text en © Börding et al. 2012 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
spellingShingle Organic Papers
Börding, Sandra
Strohmann, Carsten
Preut, Hans
Hiersemann, Martin
(4R)-4-Benzyl-3-{(4S)-4-chloro-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]butano­yl}-1,3-oxazolidin-2-one
title (4R)-4-Benzyl-3-{(4S)-4-chloro-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]butano­yl}-1,3-oxazolidin-2-one
title_full (4R)-4-Benzyl-3-{(4S)-4-chloro-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]butano­yl}-1,3-oxazolidin-2-one
title_fullStr (4R)-4-Benzyl-3-{(4S)-4-chloro-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]butano­yl}-1,3-oxazolidin-2-one
title_full_unstemmed (4R)-4-Benzyl-3-{(4S)-4-chloro-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]butano­yl}-1,3-oxazolidin-2-one
title_short (4R)-4-Benzyl-3-{(4S)-4-chloro-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]butano­yl}-1,3-oxazolidin-2-one
title_sort (4r)-4-benzyl-3-{(4s)-4-chloro-4-[(s)-2,2-dimethyl-1,3-dioxolan-4-yl]butano­yl}-1,3-oxazolidin-2-one
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3254509/
https://www.ncbi.nlm.nih.gov/pubmed/22259453
http://dx.doi.org/10.1107/S1600536811053840
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AT preuthans 4r4benzyl34s4chloro4s22dimethyl13dioxolan4ylbutanoyl13oxazolidin2one
AT hiersemannmartin 4r4benzyl34s4chloro4s22dimethyl13dioxolan4ylbutanoyl13oxazolidin2one

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