Hydrolase-mediated resolution of the hemiacetal in 2-chromanols: The impact of remote substitution

Declan P. Gavin; Aoife Foley; Thomas S. Moody; U. B. Rao Khandavilli; Simon E. Lawrence; Pat O'Neill; Anita R. Maguire

doi:10.1016/j.tetasy.2017.04.001

Hydrolase-mediated resolution of the hemiacetal in 2-chromanols: The impact of remote substitution

Declan P. Gavin
, Aoife Foley
, Thomas S. Moody
, U. B. Rao Khandavilli
, Simon E. Lawrence
, Pat O'Neill
, Anita R. Maguire

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

Abstract

Hydrolase-catalysed dynamic kinetic resolutions of chroman-2-ol and 3-methyl chroman-2-ol can be effected with up to 88% conversion and 92% ee through the use of organic solvents. Extension to the resolution of the tolterodine precursor 1 proved more challenging. The presence of the remote phenyl substituent had a significant impact on the resolution and it was not possible to achieve high enantioselectivity together with efficient conversion from the focussed panel of enzymes screened.

Original language	English
Pages (from-to)	577-585
Number of pages	9
Journal	Tetrahedron Asymmetry
Volume	28
Issue number	4
DOIs	https://doi.org/10.1016/j.tetasy.2017.04.001
Publication status	Published - 2017

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title = "Hydrolase-mediated resolution of the hemiacetal in 2-chromanols: The impact of remote substitution",

abstract = "Hydrolase-catalysed dynamic kinetic resolutions of chroman-2-ol and 3-methyl chroman-2-ol can be effected with up to 88\% conversion and 92\% ee through the use of organic solvents. Extension to the resolution of the tolterodine precursor 1 proved more challenging. The presence of the remote phenyl substituent had a significant impact on the resolution and it was not possible to achieve high enantioselectivity together with efficient conversion from the focussed panel of enzymes screened.",

author = "Gavin, \{Declan P.\} and Aoife Foley and Moody, \{Thomas S.\} and \{Rao Khandavilli\}, \{U. B.\} and Lawrence, \{Simon E.\} and Pat O'Neill and Maguire, \{Anita R.\}",

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

year = "2017",

doi = "10.1016/j.tetasy.2017.04.001",

language = "English",

volume = "28",

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journal = "Tetrahedron Asymmetry",

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TY - JOUR

T1 - Hydrolase-mediated resolution of the hemiacetal in 2-chromanols

T2 - The impact of remote substitution

AU - Gavin, Declan P.

AU - Foley, Aoife

AU - Moody, Thomas S.

AU - Rao Khandavilli, U. B.

AU - Lawrence, Simon E.

AU - O'Neill, Pat

AU - Maguire, Anita R.

PY - 2017

Y1 - 2017

N2 - Hydrolase-catalysed dynamic kinetic resolutions of chroman-2-ol and 3-methyl chroman-2-ol can be effected with up to 88% conversion and 92% ee through the use of organic solvents. Extension to the resolution of the tolterodine precursor 1 proved more challenging. The presence of the remote phenyl substituent had a significant impact on the resolution and it was not possible to achieve high enantioselectivity together with efficient conversion from the focussed panel of enzymes screened.

AB - Hydrolase-catalysed dynamic kinetic resolutions of chroman-2-ol and 3-methyl chroman-2-ol can be effected with up to 88% conversion and 92% ee through the use of organic solvents. Extension to the resolution of the tolterodine precursor 1 proved more challenging. The presence of the remote phenyl substituent had a significant impact on the resolution and it was not possible to achieve high enantioselectivity together with efficient conversion from the focussed panel of enzymes screened.

UR - https://www.scopus.com/pages/publications/85017544572

U2 - 10.1016/j.tetasy.2017.04.001

DO - 10.1016/j.tetasy.2017.04.001

M3 - Article

AN - SCOPUS:85017544572

SN - 0957-4166

VL - 28

SP - 577

EP - 585

JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

IS - 4

ER -

Hydrolase-mediated resolution of the hemiacetal in 2-chromanols: The impact of remote substitution

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