Best practice considerations for using the selectivity factor, s, as a metric for the efficiency of kinetic resolutions

Mark D. Greenhalgh; James E. Taylor; Andrew D. Smith

doi:10.1016/j.tet.2018.05.069

Best practice considerations for using the selectivity factor, s, as a metric for the efficiency of kinetic resolutions

Mark D. Greenhalgh, James E. Taylor, Andrew D. Smith

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Abstract

The suitability of using the selectivity factor, s, as a reaction metric for kinetic resolution reactions and the errors associated with its measurement are considered. Investigation of the analytical error associated with HPLC analysis of a kinetic resolution reveals that one of the largest potential sources of variation arises from the ability of a practitioner to integrate the peaks from a single analysis. The consequences of this error on the reliability of reported s values are discussed, and some general rules for good practice regarding the use and reporting of s as a metric are suggested.

Original language	English
Pages (from-to)	5554-5560
Number of pages	7
Journal	Tetrahedron
Volume	74
Issue number	38
Early online date	25 May 2018
DOIs	https://doi.org/10.1016/j.tet.2018.05.069
Publication status	Published - 20 Sept 2018

Keywords

Kinetic resolution
Selectivity factor
Data analysis
Error calculations
HPLC analysis

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10.1016/j.tet.2018.05.069

Smith_2018_Tetra_BestPractice-s-KinRes_AAM
Crown Copyright © 2018 Published by Elsevier Ltd. All rights reserved. This work has been made available online in accordance with the publisher’s policies. This is the author created accepted version manuscript following peer review and as such may differ slightly from the final published version. The final published version of this work is available at https://doi.org/10.1016/j.tet.2018.05.069
Accepted author manuscript, 844 KBLicence: CC BY-NC-ND

Catalytic Activation: Catalytic Activation of Carboxylic Acids and Alcohols
Taylor, J. E. (PI)
The Leverhulme Trust
1/05/15 → 30/04/18
Project: Fellowship
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
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

Cite this

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title = "Best practice considerations for using the selectivity factor, s, as a metric for the efficiency of kinetic resolutions",

abstract = "The suitability of using the selectivity factor, s, as a reaction metric for kinetic resolution reactions and the errors associated with its measurement are considered. Investigation of the analytical error associated with HPLC analysis of a kinetic resolution reveals that one of the largest potential sources of variation arises from the ability of a practitioner to integrate the peaks from a single analysis. The consequences of this error on the reliability of reported s values are discussed, and some general rules for good practice regarding the use and reporting of s as a metric are suggested.",

keywords = "Kinetic resolution, Selectivity factor, Data analysis, Error calculations, HPLC analysis",

author = "Greenhalgh, {Mark D.} and Taylor, {James E.} and Smith, {Andrew D.}",

note = "The research leading to these results has received funding from the ERC under the European Union{\textquoteright}s Seventh Framework Programme (FP7/2007--2013)/E.R.C. grant agreement 279850. J.E.T. thanks The Leverhulme Trust [Early Career Fellowship ECF-2014-005] for financial support. A.D.S. thanks the Royal Society for a Wolfson Merit Award.",

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T1 - Best practice considerations for using the selectivity factor, s, as a metric for the efficiency of kinetic resolutions

AU - Greenhalgh, Mark D.

AU - Taylor, James E.

AU - Smith, Andrew D.

N1 - The research leading to these results has received funding from the ERC under the European Union’s Seventh Framework Programme (FP7/2007--2013)/E.R.C. grant agreement 279850. J.E.T. thanks The Leverhulme Trust [Early Career Fellowship ECF-2014-005] for financial support. A.D.S. thanks the Royal Society for a Wolfson Merit Award.

PY - 2018/9/20

Y1 - 2018/9/20

N2 - The suitability of using the selectivity factor, s, as a reaction metric for kinetic resolution reactions and the errors associated with its measurement are considered. Investigation of the analytical error associated with HPLC analysis of a kinetic resolution reveals that one of the largest potential sources of variation arises from the ability of a practitioner to integrate the peaks from a single analysis. The consequences of this error on the reliability of reported s values are discussed, and some general rules for good practice regarding the use and reporting of s as a metric are suggested.

AB - The suitability of using the selectivity factor, s, as a reaction metric for kinetic resolution reactions and the errors associated with its measurement are considered. Investigation of the analytical error associated with HPLC analysis of a kinetic resolution reveals that one of the largest potential sources of variation arises from the ability of a practitioner to integrate the peaks from a single analysis. The consequences of this error on the reliability of reported s values are discussed, and some general rules for good practice regarding the use and reporting of s as a metric are suggested.

KW - Kinetic resolution

KW - Selectivity factor

KW - Data analysis

KW - Error calculations

KW - HPLC analysis

U2 - 10.1016/j.tet.2018.05.069

DO - 10.1016/j.tet.2018.05.069

M3 - Article

SN - 0040-4020

VL - 74

SP - 5554

EP - 5560

JO - Tetrahedron

JF - Tetrahedron

IS - 38

ER -

Best practice considerations for using the selectivity factor, s, as a metric for the efficiency of kinetic resolutions

Abstract

Keywords

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Projects

Catalytic Activation: Catalytic Activation of Carboxylic Acids and Alcohols

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

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

Cite this