174754-57-5Relevant articles and documents
Stereoselective synthesis of thienyl and furyl analogues of ephedrine
Effenberger, Franz,Eichhorn, Joachim
, p. 469 - 476 (2007/10/03)
The stereoselective syntheses of thienyl and furyl analogues of ephedrine starting from (R)- and (S)-cyanohydrins, respectively, are described. Addition of methyl Grignard to the O-trimethylsilyl protected optically active cyanohydrins (R)- and (S)-3 and hydrogenation of the resulting imino intermediates gives the erythro-2-amino alcohols 4 with high diastereoselectivity. Their reductive methylation leads to the enantiomerically pure thiophene analogues (1S,2S)- and (1R,2R)-6a, (1R,2S)- and (1S,2R)-6b as well as to the furan analogues (1S,2S)-6c and (1R,2S)-6d of ephedrine, The biological activity of the new compounds is under investigation.
Preparation of optically active cyanohydrins using the (S)-hydroxynitrile lyase from Hevea brasiliensis
Schmidt, Michael,Herve, Stephanie,Klempier, Norbert,Griengl, Herfried
, p. 7833 - 7840 (2007/10/03)
Several aliphatic, aromatic and heteroaromatic aldehydes have been converted into the chiral cyanohydrins using the (S) hydroxynitrile lyase from Hevea brasiliensis. The corresponding cyanohydrins were obtained in moderate to good yield and high enantiomeric excess with the exeption of phenyloxyacetaldehyde, benzyloxyacetaldehyde and the pyrrole-, pyridine- and indolealdehydes investigated. In contrast to previously reported results, cinnamaldehyde could be converted into (S)-(-)-2-hydroxy-4-phenyl-(E)-but-3- enenitrile with good selectivity by means of optimized reaction conditions.
Ueber die erste rekombinante Hydroxynitril-Lyase und ihre Anwendung in der Synthese von (S)-Cyanhydrinen
Foerster, Siegfried,Roos, Juergen,Effenberger, Franz,Wajant, Harald,Sprauer, Achim
, p. 493 - 494 (2007/10/03)
Keywords: Asymmetrische Synthesen; (S)-Cyanhydrine; Enzymkatalyse; Lyasen