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Milner S.E.,University College Cork | Moody T.S.,Biocatalysis Group | Maguire A.R.,University College Cork
European Journal of Organic Chemistry | Year: 2012

Enantiopure β-nitro alcohols are key chiral building blocks for the synthesis of bioactive pharmaceutical ingredients. The preparation of these target compounds in optically pure form has been the focus of much research and there has been an emergence of biocatalytic protocols in the past decade. For the first time, these biotransformations are the focus of this review. Herein, we describe two principal biocatalytic approaches to the Henry (nitroaldol) reaction. The first method is a direct enzyme-catalysed carbon-carbon bond formation resulting in either an enantio-enriched or enantiopure β-nitro alcohol. The second approach describes the Henry reaction without stereocontrol followed by a biocatalytic resolution to yield the enantiopure β-nitro alcohol. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. Source


Milner S.E.,University College Cork | Brossat M.,Biocatalysis Group | Moody T.S.,Biocatalysis Group | Elcoate C.J.,University College Cork | And 2 more authors.
Tetrahedron Asymmetry | Year: 2010

The kinetic bioresolution of 2-nitrocyclohexanol 1 was investigated by screening a range of hydrolases both for enantioselective transesterification and for enantioselective hydrolysis of the corresponding acetate. By appropriate choice of biocatalyst and conditions, both enantiomers of cis and trans 2-nitrocyclohexanol 1 can be accessed in enantiopure form. © 2010 Elsevier Ltd. All rights reserved. Source


Deasy R.E.,University College Cork | Brossat M.,Biocatalysis Group | Moody T.S.,Biocatalysis Group | Maguire A.R.,University College Cork
Tetrahedron Asymmetry | Year: 2011

Hydrolase catalysed kinetic resolutions leading to a series of 3-aryl alkanoic acids (≥94% ee) are described. Hydrolysis of the ethyl esters with a series of hydrolases was undertaken to identify biocatalysts that yield the corresponding acids with excellent enantiopurity in each case. Steric and electronic effects on the efficiency and enantioselectivity of the biocatalytic transformation were also explored. © 2011 Elsevier Ltd. All rights reserved. Source


Maguire N.M.,University College Cork | Ford A.,University College Cork | Clarke S.L.,University College Cork | Eccles K.S.,University College Cork | And 4 more authors.
Tetrahedron Asymmetry | Year: 2011

The preparation of enantiopure cyanohydrin acetates via enzymatic hydrolysis has been investigated by screening a range of biocatalysts and reaction conditions. Enzymatic resolution has been optimised through variation of the hydrolase biocatalyst and reaction conditions leading to synthetically useful routes to enantiopure cyanohydrin acetates. © 2011 Elsevier Ltd. All rights reserved. Source


Mangan D.,Biocatalysis Group | Miskelly I.,Biocatalysis Group | Moody T.S.,Biocatalysis Group
Advanced Synthesis and Catalysis | Year: 2012

The use of ene-reductase (ERED) enzymes for the asymmetric reduction of olefins offers a green, renewable alternative to metal-catalysed asymmetric reduction. We report herein the first example of an ERED-catalysed enantiospecific reduction carried out at large scale using a carbonyl reductase (CRED) enzyme in the cofactor recycle. This reaction has been paired with a hydrolase-mediated regioselective ester hydrolysis to generate a valuable chiral building block using a straightforward one-pot process. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. Source

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