Synthesis and use of alpha-silyl-substituted alpha-hydroxyacetic acids.
[reaction: see text] Rhodium-catalyzed oxygen transfer was used to generate benzyl 2-silyl-2-oxoacetates in good yields. The hydrogenation of these compounds led to chiral alpha-silyl-substituted alpha-hydroxyacetic acids. Resolution by means of HPLC using a chiral stationary phase afforded an enantiomerically pure representative of this class of compounds, which was successfully applied as a chiral ligand in an asymmetric aldol-type reaction.
Bolm
Carsten
C
Institute of Organic Chemistry, RWTH Aachen, Professor-Pirlet-Str. 1, D-52056 Aachen, Germany. carsten.bolm@oc.rwth-aachen.de
Kasyan
Andrey
A
Heider
Peter
P
Saladin
Sandra
S
Drauz
Karlheinz
K
Günther
Kurt
K
Wagner
Christoph
C
D001685:Biological Factors / Q000138:chemical synthesis; D002384:Catalysis; D018360:Crystallography, X-Ray; D006016:Glycolates / Q000138:chemical synthesis*; D008024:Ligands; D015394:Molecular Structure; D012821:Silanes / Q000737:chemistry
D001685:Biological Factors; D006016:Glycolates; D008024:Ligands; D012821:Silanes; C031149:glycolic acid