Deracemization of a Racemic Allylic Sulfoxide Using Viedma Ripening

Anthonius H. J. Engwerda; Niels Koning; Paul Tinnemans; Hugo Meekes; F. Matthias Bickelhaupt; Floris P. J. T. Rutjes; Elias Vlieg

doi:10.1021/acs.cgd.7b00828

Deracemization of a Racemic Allylic Sulfoxide Using Viedma Ripening

Anthonius H. J. Engwerda, Niels Koning, Paul Tinnemans, Hugo Meekes^*, F. Matthias Bickelhaupt, Floris P. J. T. Rutjes, Elias Vlieg

^*Corresponding author for this work

Research output: Contribution to Journal › Article › Academic › peer-review

Abstract

Despite the importance of enantiopure chiral sulfoxides, few methods exist that allow for their deracemization. Here, we show that an enantiopure sulfoxide can be produced from the corresponding racemate using Viedma ripening involving rearrangement-induced racemization. The suitable candidate for Viedma ripening was identified from a library of 24 chiral sulfoxides through X-ray structure determination. Starting from the racemic sulfoxide, an unprecedented application of a 2,3-sigmatropic rearrangement type racemization in a Viedma ripening process allowed for complete deracemization.

Original language	English
Pages (from-to)	4454-4457
Number of pages	4
Journal	Crystal Growth and Design
Volume	17
Issue number	8
DOIs	https://doi.org/10.1021/acs.cgd.7b00828
Publication status	Published - 2 Aug 2017

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10.1021/acs.cgd.7b00828

CCDC 1528086: Experimental Crystal Structure Determination
Engwerda, A. H. J. (Contributor), Koning, N. (Contributor), Tinnemans, P. (Contributor), Meekes, H. (Contributor), Bickelhaupt, F. M. (Contributor), Rutjes, F. P. J. T. (Contributor) & Vlieg, E. (Contributor), Unknown Publisher, 2 Aug 2017
DOI: 10.5517/ccdc.csd.cc1n9335, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1n9335&sid=DataCite
Dataset
CCDC 1528087: Experimental Crystal Structure Determination
Engwerda, A. H. J. (Contributor), Koning, N. (Contributor), Tinnemans, P. (Contributor), Meekes, H. (Contributor), Bickelhaupt, F. M. (Contributor), Rutjes, F. P. J. T. (Contributor) & Vlieg, E. (Contributor), Unknown Publisher, 2 Aug 2017
DOI: 10.5517/ccdc.csd.cc1n9346, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1n9346&sid=DataCite
Dataset
CCDC 1528089: Experimental Crystal Structure Determination
Engwerda, A. H. J. (Contributor), Koning, N. (Contributor), Tinnemans, P. (Contributor), Meekes, H. (Contributor), Bickelhaupt, F. M. (Contributor), Rutjes, F. P. J. T. (Contributor) & Vlieg, E. (Contributor), Unknown Publisher, 2 Aug 2017
DOI: 10.5517/ccdc.csd.cc1n9368, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1n9368&sid=DataCite
Dataset

Cite this

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title = "Deracemization of a Racemic Allylic Sulfoxide Using Viedma Ripening",

abstract = "Despite the importance of enantiopure chiral sulfoxides, few methods exist that allow for their deracemization. Here, we show that an enantiopure sulfoxide can be produced from the corresponding racemate using Viedma ripening involving rearrangement-induced racemization. The suitable candidate for Viedma ripening was identified from a library of 24 chiral sulfoxides through X-ray structure determination. Starting from the racemic sulfoxide, an unprecedented application of a 2,3-sigmatropic rearrangement type racemization in a Viedma ripening process allowed for complete deracemization.",

author = "Engwerda, {Anthonius H. J.} and Niels Koning and Paul Tinnemans and Hugo Meekes and Bickelhaupt, {F. Matthias} and Rutjes, {Floris P. J. T.} and Elias Vlieg",

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language = "English",

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AU - Engwerda, Anthonius H. J.

AU - Koning, Niels

AU - Tinnemans, Paul

AU - Meekes, Hugo

AU - Bickelhaupt, F. Matthias

AU - Rutjes, Floris P. J. T.

AU - Vlieg, Elias

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N2 - Despite the importance of enantiopure chiral sulfoxides, few methods exist that allow for their deracemization. Here, we show that an enantiopure sulfoxide can be produced from the corresponding racemate using Viedma ripening involving rearrangement-induced racemization. The suitable candidate for Viedma ripening was identified from a library of 24 chiral sulfoxides through X-ray structure determination. Starting from the racemic sulfoxide, an unprecedented application of a 2,3-sigmatropic rearrangement type racemization in a Viedma ripening process allowed for complete deracemization.

AB - Despite the importance of enantiopure chiral sulfoxides, few methods exist that allow for their deracemization. Here, we show that an enantiopure sulfoxide can be produced from the corresponding racemate using Viedma ripening involving rearrangement-induced racemization. The suitable candidate for Viedma ripening was identified from a library of 24 chiral sulfoxides through X-ray structure determination. Starting from the racemic sulfoxide, an unprecedented application of a 2,3-sigmatropic rearrangement type racemization in a Viedma ripening process allowed for complete deracemization.

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Deracemization of a Racemic Allylic Sulfoxide Using Viedma Ripening

Abstract

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Datasets

CCDC 1528086: Experimental Crystal Structure Determination

CCDC 1528087: Experimental Crystal Structure Determination

CCDC 1528089: Experimental Crystal Structure Determination

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