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Hydroxynitrile Lyase‐Catalyzed Enzymatic Nitroaldol (Henry) Reaction
Author(s) -
GruberKhadjawi Mandana,
Purkarthofer Thomas,
Skranc Wolfgang,
Griengl Herfried
Publication year - 2007
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200700064
Subject(s) - nitroaldol reaction , nitroethane , chemistry , nitromethane , catalysis , enantiomeric excess , organic chemistry , cleavage (geology) , lyase , enzyme , enzyme catalysis , nitro , enantioselective synthesis , alkyl , geotechnical engineering , fracture (geology) , engineering
The hydroxynitrile lyase from Hevea brasiliensis not only catalyzes – according to the natural activity of this enzyme – the formation and cleavage of cyanohydrins but also the reaction of nitroalkanes with aldehydes (Henry reaction). This is the first example of an enzymatic nitroaldol reaction. With nitromethane and nitroethane a broad range of aldehydes can be transformed into the corresponding nitro alcohols in yields up to 77 % and enantiomeric excess ( ee ) up to 99 %.
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