Isothiourea-catalysed sequential kinetic resolution of acyclic (±)-1,2-diols

Siegfried Harrer; Mark D. Greenhalgh; Rifahath M. Neyyappadath; Andrew D. Smith

doi:10.1055/s-0037-1610721

Isothiourea-catalysed sequential kinetic resolution of acyclic (±)-1,2-diols

Siegfried Harrer, Mark D. Greenhalgh, Rifahath M. Neyyappadath, Andrew D. Smith

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

Abstract

The isothiourea-catalysed acylative kinetic resolution of a range of acyclic (±)-1,2-diols using 1 mol% of catalyst under operationally simple conditions is reported. Significantly, the bifunctional nature of (±)-1,2-diols was exploited in a sequential double kinetic resolution, in which both kinetic resolutions operate synergistically to provide access to highly enantioenriched products. The principles that underpin this process are discussed, and selectivity factors for the individual kinetic resolution steps are reported in a model system.

Original language	English
Pages (from-to)	1555-1560
Journal	Synlett
Volume	30
Issue number	13
Early online date	10 Jul 2019
DOIs	https://doi.org/10.1055/s-0037-1610721
Publication status	Published - Aug 2019

Keywords

Kinetic resolution
Isothiourea
(±)-1,2-diols
Enantioselective acylation

Access to Document

10.1055/s-0037-1610721

Harrer_2019_Synlett_Isothiourea-catalysed_AAM
Copyright © Georg Thieme Verlag Stuttgart · New York 2019. 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://doi.org/10.1055/s-0037-1610721
Accepted author manuscript, 970 KB

RS Wolfson Merit Award: Developing Catalysis Research: New Reaction Discoveries and Practical Applications
Smith, A. D. (PI)
The Royal Society
1/01/15 → 31/12/19
Project: Fellowship
CRITICAT CDT: Critical Resource Catalysis - CRITICAT
Smith, A. D. (PI), Nolan, S. P. (CoI) & Westwood, N. J. (CoI)
EPSRC
1/05/14 → 31/10/22
Project: Standard
ERC Starting Grant EnolCat: Emulating nature: Reaction diversity and understanding through asymmetric catalysis
Smith, A. D. (PI)
European Commission
1/10/11 → 30/06/17
Project: Standard

Data underpinning "Isothiourea-Catalyzed Sequential Kinetic Resolution of Acyclic (±)-1,2-Diols"
Smith, A. D. (Creator), University of St Andrews, 9 Jan 2023
DOI: 10.17630/45a265c9-c200-47ef-979d-cb3ed157e4c0
Dataset

Cite this

@article{00c3f4322168424eb6205d825ce5faed,

title = "Isothiourea-catalysed sequential kinetic resolution of acyclic (±)-1,2-diols",

abstract = "The isothiourea-catalysed acylative kinetic resolution of a range of acyclic (±)-1,2-diols using 1 mol% of catalyst under operationally simple conditions is reported. Significantly, the bifunctional nature of (±)-1,2-diols was exploited in a sequential double kinetic resolution, in which both kinetic resolutions operate synergistically to provide access to highly enantioenriched products. The principles that underpin this process are discussed, and selectivity factors for the individual kinetic resolution steps are reported in a model system.",

keywords = "Kinetic resolution, Isothiourea, (±)-1,2-diols, Enantioselective acylation",

author = "Siegfried Harrer and Greenhalgh, {Mark D.} and Neyyappadath, {Rifahath M.} and Smith, {Andrew D.}",

note = "Authors thank the EPSRC Centre for Doctoral Training in Critical Resource Catalysis (CRITICAT, grant code EP/L016419/1, R.M.N.) for funding. We thank the European Research Council under the European Union{\textquoteright}s Seventh Framework Programme (FP7/2007–2013) ERC grant agreement no. 279850 (A.D.S.). A.D.S. thanks the Royal Society for a Wolfson Research Merit Award. ",

year = "2019",

month = aug,

doi = "10.1055/s-0037-1610721",

language = "English",

volume = "30",

pages = "1555--1560",

journal = "Synlett",

issn = "0936-5214",

publisher = "Georg Thieme Verlag",

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TY - JOUR

T1 - Isothiourea-catalysed sequential kinetic resolution of acyclic (±)-1,2-diols

AU - Harrer, Siegfried

AU - Greenhalgh, Mark D.

AU - Neyyappadath, Rifahath M.

AU - Smith, Andrew D.

N1 - Authors thank the EPSRC Centre for Doctoral Training in Critical Resource Catalysis (CRITICAT, grant code EP/L016419/1, R.M.N.) for funding. We thank the European Research Council under the European Union’s Seventh Framework Programme (FP7/2007–2013) ERC grant agreement no. 279850 (A.D.S.). A.D.S. thanks the Royal Society for a Wolfson Research Merit Award.

PY - 2019/8

Y1 - 2019/8

N2 - The isothiourea-catalysed acylative kinetic resolution of a range of acyclic (±)-1,2-diols using 1 mol% of catalyst under operationally simple conditions is reported. Significantly, the bifunctional nature of (±)-1,2-diols was exploited in a sequential double kinetic resolution, in which both kinetic resolutions operate synergistically to provide access to highly enantioenriched products. The principles that underpin this process are discussed, and selectivity factors for the individual kinetic resolution steps are reported in a model system.

AB - The isothiourea-catalysed acylative kinetic resolution of a range of acyclic (±)-1,2-diols using 1 mol% of catalyst under operationally simple conditions is reported. Significantly, the bifunctional nature of (±)-1,2-diols was exploited in a sequential double kinetic resolution, in which both kinetic resolutions operate synergistically to provide access to highly enantioenriched products. The principles that underpin this process are discussed, and selectivity factors for the individual kinetic resolution steps are reported in a model system.

KW - Kinetic resolution

KW - Isothiourea

KW - (±)-1,2-diols

KW - Enantioselective acylation

U2 - 10.1055/s-0037-1610721

DO - 10.1055/s-0037-1610721

M3 - Article

SN - 0936-5214

VL - 30

SP - 1555

EP - 1560

JO - Synlett

JF - Synlett

IS - 13

ER -

Isothiourea-catalysed sequential kinetic resolution of acyclic (±)-1,2-diols

Abstract

Keywords

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Projects

RS Wolfson Merit Award: Developing Catalysis Research: New Reaction Discoveries and Practical Applications

CRITICAT CDT: Critical Resource Catalysis - CRITICAT

ERC Starting Grant EnolCat: Emulating nature: Reaction diversity and understanding through asymmetric catalysis

Datasets

Data underpinning "Isothiourea-Catalyzed Sequential Kinetic Resolution of Acyclic (±)-1,2-Diols"

Cite this