Synthesis, Table of Contents PAPER © Georg Thieme Verlag Stuttgart · New York New Chiral Ligands Derived from Mandelic Acid: Synthesis and Application in the Asymmetric Phenyl Transfer Reaction to an Aromatic Aldehyde Carsten Bolm*, Lorenzo Zani, Jens Rudolph, Ingo SchiffersInstitut für Organische Chemie der RWTH Aachen, Professor-Pirlet-Str. 1, 52056 Aachen, GermanyFax: +49(241)8092391; e-Mail: carsten.bolm@oc.rwth-aachen.de; Recommend Article Abstract Buy Article All articles of this category Abstract Starting from inexpensive enantiopure (R)- and (S)-mandelic acid, a range of α-hydroxy-2-oxazolines has been prepared. The synthesis involves the condensation of the acid chloride with a vicinal amino alcohol, followed by intramolecular cyclization to form the oxazoline ring. The resulting compounds have been used as ligands in the asymmetric phenyl transfer reaction to 4-chlorobenzaldehyde, employing a mixture of triphenylborane and diethylzinc as the phenyl source. Good yields (up to 76%) and moderate enantioselectivities (up to 35%) have been achieved. Key words asymmetric catalysis - mandelic acid - organometallics - oxazolines - phenyl transfer - zinc Full Text References References 1a Noyori R. Asymmetric Catalysis in Organic Synthesis Wiley; New York: 1994. 1b Transition Metals for Organic Synthesis Beller M. Bolm C. Wiley-VCH; Weinheim: 1998. 1c Comprehensive Asymmetric Catalysis Jacobsen EN. Pfalz A. Yamamoto H. Springer; Berlin: 1999. 1d Catalytic Asymmetric Synthesis 2nd ed.: Ojima I. Wiley-VCH; New York: 2000. 2 Seebach D. Hungerbühler E. In Modern Synthetic Methods Scheffold R. Salle and Sauerländer; Frankfurt: 1980. p.91 3 Blaser HU. Chem. Rev. 1992, 92: 935 4a Meyers AI. Gant TG. Tetrahedron 1994, 50: 2297 4b Greene TW. Wuts PGM. Protective Groups in Organic Chemistry Wiley; New York: 1999. 5a Bolm C. Angew. Chem., Int. Ed. Engl. 1991, 30: 542 5b Pfalz A. Acc. Chem. Res. 1993, 26: 339 5c Meyers AI. J. Heterocycl. 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