New chiral ligands derived from mandelic acid: Synthesis and application in the asymmetric phenyl transfer reaction to an aromatic aldehyde

C Bolm, L Zani, J Rudolph, I Schiffers

Index: Bolm, Carsten; Zani, Lorenzo; Rudolph, Jens; Schiffers, Ingo Synthesis, 2004 , # 13 p. 2173 - 2180

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Citation Number: 16

Abstract

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 ...