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

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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. © 2004 Elsevier Ltd. All rights reserved.

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Głuszyńska, A., & Rozwadowska, M. D. (2004). Enantioselective addition of methyllithium to a prochiral imine - The substrate in the Pomeranz-Fritsch-Bobbitt synthesis of tetrahydroisoquinoline derivatives mediated by chiral monooxazolines. Tetrahedron Asymmetry, 15(20), 3289–3295. https://doi.org/10.1016/j.tetasy.2004.08.011

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