A scalable, chromatography-free synthesis of benzotetramisole

David Sydney Bernard Daniels; Siobhan Rose Smith; Tomas Lebl; P. Shapland; Andrew David Smith

doi:10.1055/s-0034-1378931

A scalable, chromatography-free synthesis of benzotetramisole

David Sydney Bernard Daniels, Siobhan Rose Smith, Tomas Lebl, P. Shapland, Andrew David Smith

Research output: Contribution to journal › Article › peer-review

Abstract

The scalable, chromatography-free synthesis of the chiral isothiourea benzotetramisole (BTM) in two steps from commercially available materials is presented. A detailed procedure for the synthesis of both enantiomers and the racemate on ca. 10 gram scale is disclosed.

Original language	English
Pages (from-to)	34-41
Journal	Synthesis
Volume	47
Issue number	1
Early online date	21 Nov 2014
DOIs	https://doi.org/10.1055/s-0034-1378931
Publication status	Published - Jan 2015

Keywords

Isothiourea
Lewis base catalysis
Asymmetric catalysis
Kinetic resolution
Rearrangement
Benzotetramisole

Access to Document

10.1055/s-0034-1378931

Smith_2015_Synthesis_Scalable_AM
© Georg Thieme Verlag Stuttgart, New York. This work is made available online in accordance with the publisher’s policies. This is the author created, accepted version manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at https://dx.doi.org/10.1055/s-0034-1378931
Accepted author manuscript, 744 KB

Cite this

@article{d9b6a498f064456f9e2cef6b24271c28,

title = "A scalable, chromatography-free synthesis of benzotetramisole",

abstract = "The scalable, chromatography-free synthesis of the chiral isothiourea benzotetramisole (BTM) in two steps from commercially available materials is presented. A detailed procedure for the synthesis of both enantiomers and the racemate on ca. 10 gram scale is disclosed.",

keywords = "Isothiourea , Lewis base catalysis, Asymmetric catalysis, Kinetic resolution, Rearrangement, Benzotetramisole ",

author = "Daniels, {David Sydney Bernard} and Smith, {Siobhan Rose} and Tomas Lebl and P. Shapland and Smith, {Andrew David}",

note = "The authors thank the Royal Society for a University Research Fellowship (ADS), the EPSRC (EP/J018139/1, DSBD), and GSK (Case award to SRS) for funding. They also thank the European Research Council under the European Union{\textquoteright}s Seventh Framework Programme (FP7/2007-2013) ERC grant agreement number 279850 for additional funding, and the EPSRC UK National Mass Spectrometry Service Centre at Swansea University. ",

year = "2015",

month = jan,

doi = "10.1055/s-0034-1378931",

language = "English",

volume = "47",

pages = "34--41",

journal = "Synthesis",

issn = "0039-7881",

publisher = "Georg Thieme Verlag",

number = "1",

}

TY - JOUR

T1 - A scalable, chromatography-free synthesis of benzotetramisole

AU - Daniels, David Sydney Bernard

AU - Smith, Siobhan Rose

AU - Lebl, Tomas

AU - Shapland, P.

AU - Smith, Andrew David

N1 - The authors thank the Royal Society for a University Research Fellowship (ADS), the EPSRC (EP/J018139/1, DSBD), and GSK (Case award to SRS) for funding. They also thank the European Research Council under the European Union’s Seventh Framework Programme (FP7/2007-2013) ERC grant agreement number 279850 for additional funding, and the EPSRC UK National Mass Spectrometry Service Centre at Swansea University.

PY - 2015/1

Y1 - 2015/1

N2 - The scalable, chromatography-free synthesis of the chiral isothiourea benzotetramisole (BTM) in two steps from commercially available materials is presented. A detailed procedure for the synthesis of both enantiomers and the racemate on ca. 10 gram scale is disclosed.

AB - The scalable, chromatography-free synthesis of the chiral isothiourea benzotetramisole (BTM) in two steps from commercially available materials is presented. A detailed procedure for the synthesis of both enantiomers and the racemate on ca. 10 gram scale is disclosed.

KW - Isothiourea

KW - Lewis base catalysis

KW - Asymmetric catalysis

KW - Kinetic resolution

KW - Rearrangement

KW - Benzotetramisole

UR - https://www.thieme-connect.de/DOI/DOI?10.1055/s-0034-1378931#supmat

U2 - 10.1055/s-0034-1378931

DO - 10.1055/s-0034-1378931

M3 - Article

AN - SCOPUS:84911940420

SN - 0039-7881

VL - 47

SP - 34

EP - 41

JO - Synthesis

JF - Synthesis

IS - 1

ER -

A scalable, chromatography-free synthesis of benzotetramisole

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Clean catalysis for sustainable develop: Clean catalysis for sustainable development

Clean catalysis for sustainable develop: Clean catalysis for sustainable development

Cite this

A scalable, chromatography-free synthesis of benzotetramisole

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Projects

Clean catalysis for sustainable develop: Clean catalysis for sustainable development

Clean catalysis for sustainable develop: Clean catalysis for sustainable development

Cite this