Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2012, Issue 16, Pages 3059-3067Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201101840
Keywords
Enzyme catalysis; Biocatalysis; C-C coupling; Nitroaldol reaction; Nitro alcohols
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Funding
- Food's Food Institutional Research Measure (FIRM) [08/RD/AFRC/673]
- Irish Research Council for Science, Engineering & Technology (IRCSET)
- Pfizer Pharmaceuticals
- European Regional Development Fund under the European Sustainable Competitiveness Program for Northern Ireland
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Enantiopure beta-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 carboncarbon bond formation resulting in either an enantio-enriched or enantiopure beta-nitro alcohol. The second approach describes the Henry reaction without stereocontrol followed by a biocatalytic resolution to yield the enantiopure beta-nitro alcohol.
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