A series of chiral monooxazoline ligands 7-24 with substituents at C-2 and C-4, differing in electronic and steric properties, has been synthesized from (+)-thiomicamine 6. The effect of the oxazoline structure on the course of addition of methyllithium to imine 1 has been studied. The addition product, amine 3, which is the key intermediate in the Pomeranz-Fritsch-Bobbitt synthesis of tetrahydroisoquinoline derivatives, has been obtained in high yield (92%) and with up to 76% ee. © 2004 Elsevier Ltd. All rights reserved.
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