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Keywords:

  • biotransformations;
  • C[BOND]C bond formation;
  • Henry reaction;
  • hydroxynitrile lyase;
  • β-nitro alcohols;
  • stereoselectivity

Abstract

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 %.