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An asymmetric synthesis of β-iodo-α-(hydroxyalkyl)acrylates has been developed involving conjugate addition of I− to menthyl propiolates to give β-iodo allenolate intermediates which undergo 1,2-addition to form β-iodo Baylis–Hillman products. Modest diastereoselectivities (37–58% de) and excellent yields (80–87%) were obtained when (1R,2S,5R)-(−)-menthol was used as a chiral auxiliary. The two diastereoisomers of the product were separated by silica gel chromatography to give diastereomerically pure products.

A series of novel planar chiral N,O-[2,2]paracyclophane ligands were synthesised and applied as catalysts in the enantioselective addition of diethylzinc to aldehydes. The results indicate that the planar chirality of [2,2]paracyclophane, not the central chirality of the oxazoline, is the dominant stereocontrolling element.