INVESTIGADORES
BISOGNO Fabricio Roman
artículos
Título:
Chemo- and Stereodivergent Preparation of Terminal Epoxides and Bromohydrins through One-Pot Biocatalysed Reactions: Access to Enantiopure Five- and Six-Membered N-Heterocycles
Autor/es:
FABRICIO R. BISOGNO; ANÍBAL CUETOS; ALEJANDRO A. ORDEN; MARCELA KURINA-SANZ; IVÁN LAVANDERA; VICENTE GOTOR
Revista:
ADVANCED SYNTHESIS & CATALYSIS (PRINT)
Editorial:
WILEY-V C H VERLAG GMBH
Referencias:
Año: 2010 vol. 352 p. 1657 - 1661
ISSN:
1615-4150
Resumen:
Different enantiopure terminal epoxides
or bromohydrins have chemoselectively been synthesised
in one-pot starting from the correspondingone-pot starting from the corresponding
a-bromo ketones through alcohol dehydrogenase
(ADH)-catalysed processes adding an organic cosolvent
and tuning appropriately the medium pH
and the temperature. Thus, at neutral pH enantiopure
bromohydrins were obtained while using basic
conditions (pH 9.510) 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.-bromo ketones through alcohol dehydrogenase
(ADH)-catalysed processes adding an organic cosolvent
and tuning appropriately the medium pH
and the temperature. Thus, at neutral pH enantiopure
bromohydrins were obtained while using basic
conditions (pH 9.510) 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.