PREPARATION OF OPTICALLY-ACTIVE CYANOHYDRINS USING THE (S)-HYDROXYNITRILE LYASE FROM HEVEA-BRASILIENSIS

Citation
M. Schmidt et al., PREPARATION OF OPTICALLY-ACTIVE CYANOHYDRINS USING THE (S)-HYDROXYNITRILE LYASE FROM HEVEA-BRASILIENSIS, Tetrahedron, 52(23), 1996, pp. 7833-7840
Citations number
45
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
ISSN journal
00404020
Volume
52
Issue
23
Year of publication
1996
Pages
7833 - 7840
Database
ISI
SICI code
0040-4020(1996)52:23<7833:POOCUT>2.0.ZU;2-D
Abstract
Several aliphatic, aromatic and heteroaromatic aldehydes have been con verted into the chiral cyanohydrins using the (S)-hydroxynitrilelyase from Hevea brasiliensis. The corresponding cyanohydrins were obtained in moderate to good yield and high enantiomeric excess with the exepti on of phenyloxyacetaldehyde, benzyloxyacetaldehyde and the pyrrole-, p yridine- and indolealdehydes investigated. In contrast to previously r eported results, cinnamaldehyde could be converted into (S)-()-2-hydro xy-4-phenyl-(E)-but-3-enenitrile with good selectivity by means of opt imized reaction conditions. Copyright (C) 1996 Elsevier Science Ltd