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(2S)-2-[(2S*,5R*,6R*)-5,6-Dimethoxy-5,6-dimethyl-1,4-dioxan-2-yl]-1-[(S)-1,1-dimethylethylsulfonyl]aziridine
The reaction of a sulfur ylide with a chiral non-racemic sulfinyl imine afforded the desired aziridine in excellent yield and subsequent oxidation of the sulfinyl moiety dissolved in anhydrous dichloromethane using a 75% aqueous solution of 3-chloroperoxybenzoic acid afforded the title compound,...
Autores principales: | , , , , |
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Formato: | Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2010
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3011582/ https://www.ncbi.nlm.nih.gov/pubmed/21589609 http://dx.doi.org/10.1107/S1600536810048816 |
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author | Moragas Solà, Toni Lewis, William Bettigeri, Sampada V. Stockman, Robert A. Forbes, David C. |
author_facet | Moragas Solà, Toni Lewis, William Bettigeri, Sampada V. Stockman, Robert A. Forbes, David C. |
author_sort | Moragas Solà, Toni |
collection | PubMed |
description | The reaction of a sulfur ylide with a chiral non-racemic sulfinyl imine afforded the desired aziridine in excellent yield and subsequent oxidation of the sulfinyl moiety dissolved in anhydrous dichloromethane using a 75% aqueous solution of 3-chloroperoxybenzoic acid afforded the title compound, C(14)H(27)NO(6)S. The configuration of the newly formed stereogenic center at the point of attachment of the 1,4-dioxane ring to the aziridine ring is S. The configurations of the pre-existing sites 2-, 5-, and 6-positions of the 1,4-dioxane ring prior to reaction of sulfinyl imine with the sulfur ylide are S, R, and R, respectively. The C—N bond lengths of the aziridine are 1.478 (2) and 1.486 (2) Å. |
format | Text |
id | pubmed-3011582 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2010 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-30115822010-12-30 (2S)-2-[(2S*,5R*,6R*)-5,6-Dimethoxy-5,6-dimethyl-1,4-dioxan-2-yl]-1-[(S)-1,1-dimethylethylsulfonyl]aziridine Moragas Solà, Toni Lewis, William Bettigeri, Sampada V. Stockman, Robert A. Forbes, David C. Acta Crystallogr Sect E Struct Rep Online Organic Papers The reaction of a sulfur ylide with a chiral non-racemic sulfinyl imine afforded the desired aziridine in excellent yield and subsequent oxidation of the sulfinyl moiety dissolved in anhydrous dichloromethane using a 75% aqueous solution of 3-chloroperoxybenzoic acid afforded the title compound, C(14)H(27)NO(6)S. The configuration of the newly formed stereogenic center at the point of attachment of the 1,4-dioxane ring to the aziridine ring is S. The configurations of the pre-existing sites 2-, 5-, and 6-positions of the 1,4-dioxane ring prior to reaction of sulfinyl imine with the sulfur ylide are S, R, and R, respectively. The C—N bond lengths of the aziridine are 1.478 (2) and 1.486 (2) Å. International Union of Crystallography 2010-11-27 /pmc/articles/PMC3011582/ /pubmed/21589609 http://dx.doi.org/10.1107/S1600536810048816 Text en © Moragas Solà et al. 2010 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 Moragas Solà, Toni Lewis, William Bettigeri, Sampada V. Stockman, Robert A. Forbes, David C. (2S)-2-[(2S*,5R*,6R*)-5,6-Dimethoxy-5,6-dimethyl-1,4-dioxan-2-yl]-1-[(S)-1,1-dimethylethylsulfonyl]aziridine |
title | (2S)-2-[(2S*,5R*,6R*)-5,6-Dimethoxy-5,6-dimethyl-1,4-dioxan-2-yl]-1-[(S)-1,1-dimethylethylsulfonyl]aziridine |
title_full | (2S)-2-[(2S*,5R*,6R*)-5,6-Dimethoxy-5,6-dimethyl-1,4-dioxan-2-yl]-1-[(S)-1,1-dimethylethylsulfonyl]aziridine |
title_fullStr | (2S)-2-[(2S*,5R*,6R*)-5,6-Dimethoxy-5,6-dimethyl-1,4-dioxan-2-yl]-1-[(S)-1,1-dimethylethylsulfonyl]aziridine |
title_full_unstemmed | (2S)-2-[(2S*,5R*,6R*)-5,6-Dimethoxy-5,6-dimethyl-1,4-dioxan-2-yl]-1-[(S)-1,1-dimethylethylsulfonyl]aziridine |
title_short | (2S)-2-[(2S*,5R*,6R*)-5,6-Dimethoxy-5,6-dimethyl-1,4-dioxan-2-yl]-1-[(S)-1,1-dimethylethylsulfonyl]aziridine |
title_sort | (2s)-2-[(2s*,5r*,6r*)-5,6-dimethoxy-5,6-dimethyl-1,4-dioxan-2-yl]-1-[(s)-1,1-dimethylethylsulfonyl]aziridine |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3011582/ https://www.ncbi.nlm.nih.gov/pubmed/21589609 http://dx.doi.org/10.1107/S1600536810048816 |
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