Chemo- and Stereodivergent Preparation of Terminal Epoxides and Bromohydrins through One-Pot Biocatalysed Reactions: Access to Enantiopure Five- and Six-Membered N-Heterocycles

Different enantiopure terminal epoxides or bromohydrins have chemoselectively been synthesised in one‐pot starting from the corresponding α‐bromo ketones through alcohol dehydrogenase (ADH)‐catalysed processes adding an organic co‐solvent and tuning appropriately the medium pH and the temperature. T...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2010-07, Vol.352 (10), p.1657-1661
Main Authors: Bisogno, Fabricio R., Cuetos, Aníbal, Orden, Alejandro A., Kurina-Sanz, Marcela, Lavandera, Iván, Gotor, Vicente
Format: Article
Language:English
Subjects:
Alcohol dehydrogenase
alcohol dehydrogenases
bromohydrins
Catalysis
epoxides
Ketones
medium engineering
one-pot reaction
prolinol
Synthesis
Terminals
Transformations
Tuning
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Summary:Different enantiopure terminal epoxides or bromohydrins have chemoselectively been synthesised in one‐pot starting from the corresponding α‐bromo ketones through alcohol dehydrogenase (ADH)‐catalysed processes adding an organic co‐solvent and tuning appropriately the medium pH and the temperature. Thus, at neutral pH enantiopure bromohydrins were obtained while using basic conditions (pH 9.5–10) epoxides were isolated as the main product. Furthermore, by simple selection of the biocatalyst, chemo‐ and stereodivergent transformations were achieved to obtain, e.g., enantiopure prolinol or piperidin‐3‐ol.
ISSN:1615-4150
1615-4169
1615-4169
DOI:10.1002/adsc.201000353