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Enantioselective addition of methyllithium to a prochiral imine—the substrate in the Pomeranz–Fritsch–Bobbitt synthesis of tetrahydroisoquinoline derivatives mediated by chiral monooxazolines

Authors
Publisher
Elsevier Ltd
Publication Date
Volume
15
Issue
20
Identifiers
DOI: 10.1016/j.tetasy.2004.08.011

Abstract

Abstract 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.

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