Enantioselective Addition of Organolithium Reagents to Imines Mediated by C2-Symmetric Bis(aziridine) Ligands

F. Johansson, David Ackland Tanner

    Research output: Contribution to journalJournal articleResearchpeer-review

    Abstract

    The C-2-symmetric bis(aziridine) ligands 1 - 5 have been screened in the enantioselective addition of organolithium reagents to imines. Ligand 1 (used in stoichiometric amounts) was found to be superior in terms of chemical yield and enantioselectivity, the best result being 90% yield and 89% e.e. in the addition of vinyllithium to imine 6a. Use of ligand 1 in substoichiometric amounts gave poorer yield and lower enantioselectivity. The enantioselectivity of the reaction was investigated as a function of substrate, reagent, stoichiometry and temperature, but no firm mechanistic conclusions could be drawn. Preliminary results with deuterium-labelled methyllithium indicate complexation/exchange processes involving ligand, reagent and substrate. (C) 1998 Elsevier Science Ltd. All rights reserved.
    Original languageEnglish
    JournalTetrahedron
    Volume54
    Issue number38
    Pages (from-to)11549-11566
    ISSN0040-4020
    DOIs
    Publication statusPublished - 1998

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