C. Bolm, L. Zani, J. Rudolph
Sep 1, 2004
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Synthesis
Abstract
Starting from inexpensive enantiopure (R)- and (S)-mandelic acid, a range of u-hydroxy-2-oxazolines has been prepared. The synthesis involves the condensation of the acid chloride with a vicinal amino alcohol, followed byintramolecular 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.