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

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

Access to Document

10.1021/acs.cgd.7b00828

Handle.net

Persistent link

Cite this

@article{c9e9b683161740f8865c354a6222c6aa,

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",

year = "2017",

month = aug,

day = "2",

doi = "10.1021/acs.cgd.7b00828",

language = "English",

volume = "17",

pages = "4454--4457",

journal = "Crystal Growth and Design",

issn = "1528-7483",

publisher = "American Chemical Society",

number = "8",

}

TY - JOUR

T1 - Deracemization of a Racemic Allylic Sulfoxide Using Viedma Ripening

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

PY - 2017/8/2

Y1 - 2017/8/2

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.

UR - http://www.scopus.com/inward/record.url?scp=85026860592&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85026860592&partnerID=8YFLogxK

U2 - 10.1021/acs.cgd.7b00828

DO - 10.1021/acs.cgd.7b00828

M3 - Article

AN - SCOPUS:85026860592

SN - 1528-7483

VL - 17

SP - 4454

EP - 4457

JO - Crystal Growth and Design

JF - Crystal Growth and Design

IS - 8

ER -

Deracemization of a Racemic Allylic Sulfoxide Using Viedma Ripening

Abstract

UN SDGs

Access to Document

Handle.net

Other files and links

Fingerprint

CCDC 1528092: Experimental Crystal Structure Determination

CCDC 1528095: Experimental Crystal Structure Determination

CCDC 1528096: Experimental Crystal Structure Determination

Cite this

Deracemization of a Racemic Allylic Sulfoxide Using Viedma Ripening

Abstract

UN SDGs

Access to Document

Handle.net

Other files and links

Fingerprint

Datasets

CCDC 1528092: Experimental Crystal Structure Determination

CCDC 1528095: Experimental Crystal Structure Determination

CCDC 1528096: Experimental Crystal Structure Determination

Cite this