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Synfacts 2006(7): 0723-0723
DOI: 10.1055/s-2006-941912
DOI: 10.1055/s-2006-941912
Bioorganic Chemistry and Organocatalysis
© Georg Thieme Verlag Stuttgart · New York
Biocatalytic Asymmetric Henry Reaction
T. Purkarthofer, K. Gruber, M. Gruber-Khadjawi, K. Waich, W. Skranc, D. Mink, H. Griengl*
Research Centre Applied Biocatalysis, Graz and DSM Fine Chemicals, Linz, Austria; DSM Research, Geleen, The Netherlands
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
22. Juni 2006 (online)
Significance
The first biocatalytic asymmetric Henry reaction has been described. Addition of nitroalkanes 2 to aldehydes 1 in the presence of hydroxynitrile lyase from Hevea brasiliensis (HbHNL) gives nitroalcohols 3 in good yields, enantioselectivities, and diastereoselectivities. Both aromatic and aliphatic aldehydes can be used. Furthermore, mechanistic investigations based on molecular modeling as well as kinetic experiments are provided.