ASYMMETRIC HYDROCYANATION OF ALDEHYDES WITH CYCLO-DIPEPTIDES - A NEW MECHANISTIC APPROACH

Authors
SHVO Y GAL M BECKER Y ELGAVI A
Citation
Y. Shvo et al., ASYMMETRIC HYDROCYANATION OF ALDEHYDES WITH CYCLO-DIPEPTIDES - A NEW MECHANISTIC APPROACH, Tetrahedron : asymmetry, 7(3), 1996, pp. 911-924
Citations number
41
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
7
Issue
3
Year of publication
1996
Pages
911 - 924
Database
ISI
SICI code
0957-4166(1996)7:3<911:AHOAWC>2.0.ZU;2-D
Abstract
A new mechanistic suggestion for the asymmetric hydrocyanation reactio n of aldehydes with cyclo[-(S)-phenylalanyl-(S)-histidyl] (CPH) as cat alyst is presented. Kinetic measurements indicate a second order react ion in the cyclopeptide catalyst. A heterogeneous hydrogen bonded poly mer of CPH is considered to be the reactive state of the catalyst wher e two adjacent imidazole bases function as the reactive sites, This st ructural proposition is also supported by MNDO calculations performed on a dimer of CPH. (C) 1996 Elsevier Science Ltd