title: Synthesis and use of alpha-silyl-substituted alpha-hydroxyacetic acids.
abstract: [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.
authors.affiliation: Institute of Organic Chemistry, RWTH Aachen, Professor-Pirlet-Str. 1, D-52056 Aachen, Germany. carsten.bolm@oc.rwth-aachen.de
authors.forename: Carsten
authors.initials: C
authors.lastname: Bolm
authors.forename: Andrey
authors.initials: A
authors.lastname: Kasyan
authors.forename: Peter
authors.initials: P
authors.lastname: Heider
authors.forename: Sandra
authors.initials: S
authors.lastname: Saladin
authors.forename: Karlheinz
authors.initials: K
authors.lastname: Drauz
authors.forename: Kurt
authors.initials: K
authors.lastname: Günther
authors.forename: Christoph
authors.initials: C
authors.lastname: Wagner
mesh_terms: 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
chemical_list: D001685:Biological Factors; D006016:Glycolates; D008024:Ligands; D012821:Silanes; C031149:glycolic acid