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Carbohydrates as Building Blocks of Privileged Ligands for Multiphasic Asymmetric Catalysis
Author(s) -
Benessere Vincenzo,
De Roma Antonella,
Ruffo Francesco
Publication year - 2008
Publication title -
chemsuschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.412
H-Index - 157
eISSN - 1864-564X
pISSN - 1864-5631
DOI - 10.1002/cssc.200800013
Subject(s) - catalysis , desymmetrization , homogeneous , enantioselective synthesis , chemistry , ligand (biochemistry) , homogeneous catalysis , combinatorial chemistry , organic chemistry , mathematics , receptor , combinatorics , biochemistry
Abstract To combine the high chemical performance of asymmetric catalysis with the increasing need for sustainability, a strategy is presented that involves the straightforward preparation of “Trost”‐like ligands suitable for application in multiphasic homogeneous catalysis. Ligands with coordinating functions (phosphinoamide‐phoshinoester groups) as well as phase tags introduced on a D ‐glucose scaffold were prepared and then examined in the Pd‐catalysed asymmetric desymmetrization of meso‐2‐cyclopenten‐1,4‐diol biscarbamate. In line with our assumption, the performance of the catalyst system under traditional conditions is as high as that of the original Trost ligand, derived from trans‐cyclohexanediamine, giving enantioselectivities of 98 % ee. Moreover, promising results were observed under multiphasic homogeneous conditions.