Impact of variation of the acyl group on the efficiency and selectivity of the lipase-mediated resolution of 2-phenylalkanols

Aoife M. Foley; Declan P. Gavin; Ilona Joniec; Anita R. Maguire

doi:10.1016/j.tetasy.2017.08.002

Impact of variation of the acyl group on the efficiency and selectivity of the lipase-mediated resolution of 2-phenylalkanols

Aoife M. Foley
, Declan P. Gavin
, Ilona Joniec
, Anita R. Maguire

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

Abstract

By tuning the steric properties of the acyl group to control the efficiency and selectivity of the resolution, 2-phenyl-1-propanol 1a was prepared by lipase-catalysed hydrolysis using a short-chain acyl group, with E-values of up to 66 (ee up to 95%). 2-Phenylbutan-1-ol 1b was similarly resolved (up to 86% ee) using the optimised conditions, while the ester of the more sterically demanding 3-methyl-2-phenylbutan-1-ol 1c proved resistant to enzymatic hydrolysis under these conditions.

Original language	English
Pages (from-to)	1144-1153
Number of pages	10
Journal	Tetrahedron Asymmetry
Volume	28
Issue number	9
DOIs	https://doi.org/10.1016/j.tetasy.2017.08.002
Publication status	Published - 2017

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title = "Impact of variation of the acyl group on the efficiency and selectivity of the lipase-mediated resolution of 2-phenylalkanols",

abstract = "By tuning the steric properties of the acyl group to control the efficiency and selectivity of the resolution, 2-phenyl-1-propanol 1a was prepared by lipase-catalysed hydrolysis using a short-chain acyl group, with E-values of up to 66 (ee up to 95\%). 2-Phenylbutan-1-ol 1b was similarly resolved (up to 86\% ee) using the optimised conditions, while the ester of the more sterically demanding 3-methyl-2-phenylbutan-1-ol 1c proved resistant to enzymatic hydrolysis under these conditions.",

author = "Foley, \{Aoife M.\} and Gavin, \{Declan P.\} and Ilona Joniec and Maguire, \{Anita R.\}",

note = "Publisher Copyright: {\textcopyright} 2017 Elsevier Ltd",

year = "2017",

doi = "10.1016/j.tetasy.2017.08.002",

language = "English",

volume = "28",

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journal = "Tetrahedron Asymmetry",

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T1 - Impact of variation of the acyl group on the efficiency and selectivity of the lipase-mediated resolution of 2-phenylalkanols

AU - Foley, Aoife M.

AU - Gavin, Declan P.

AU - Joniec, Ilona

AU - Maguire, Anita R.

PY - 2017

Y1 - 2017

N2 - By tuning the steric properties of the acyl group to control the efficiency and selectivity of the resolution, 2-phenyl-1-propanol 1a was prepared by lipase-catalysed hydrolysis using a short-chain acyl group, with E-values of up to 66 (ee up to 95%). 2-Phenylbutan-1-ol 1b was similarly resolved (up to 86% ee) using the optimised conditions, while the ester of the more sterically demanding 3-methyl-2-phenylbutan-1-ol 1c proved resistant to enzymatic hydrolysis under these conditions.

AB - By tuning the steric properties of the acyl group to control the efficiency and selectivity of the resolution, 2-phenyl-1-propanol 1a was prepared by lipase-catalysed hydrolysis using a short-chain acyl group, with E-values of up to 66 (ee up to 95%). 2-Phenylbutan-1-ol 1b was similarly resolved (up to 86% ee) using the optimised conditions, while the ester of the more sterically demanding 3-methyl-2-phenylbutan-1-ol 1c proved resistant to enzymatic hydrolysis under these conditions.

UR - https://www.scopus.com/pages/publications/85027987055

U2 - 10.1016/j.tetasy.2017.08.002

DO - 10.1016/j.tetasy.2017.08.002

M3 - Article

AN - SCOPUS:85027987055

SN - 0957-4166

VL - 28

SP - 1144

EP - 1153

JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

IS - 9

ER -

Impact of variation of the acyl group on the efficiency and selectivity of the lipase-mediated resolution of 2-phenylalkanols

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