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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,...

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Detalles Bibliográficos
Autores principales: Moragas Solà, Toni, Lewis, William, Bettigeri, Sampada V., Stockman, Robert A., Forbes, David C.
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2010
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.
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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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