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Synlett 1992; 1992(8): 615-625
DOI: 10.1055/s-1992-21433
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The Synthetic Utility of α-Amino Alkoxides

Daniel L. Comins*
  • *Department of Chemistry, North Carolina State University, Raleigh, North Carolina 27695-8204, USA
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Publication Date:
08 March 2002 (online)

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Organic reactions involving α-amino alkoxides as intermediates are reviewed. Emphasis is placed on the author's work concerning the preparation and use of α-amino alkoxides as protective groups and metalation directors for directed lithiation reactions. 1. Introduction 2. An Alternative Preparation of α-Amino Alkoxides 3. Ortho Lithiation Directed by α-Amino Alkoxides 3.1 The Initial Studies 3.2 Rate Enhancement via Intramolecular TMEDA-Like Assisted Metalation 3.3 Low-Temperature Ortho Lithiation of Aryl α-Amino Alkoxides 3.4 Regioselective Lithiation Controlled by Varying the Amine Component of the α-Amino Alkoxide 4. Lithiation of Heterocycles Directed by α-Amino Alkoxides 4.1 Regioselective Ring Lithiation 4.2 N-Methyl Lithiation of N-Methylpyrroles 4.3 N-Methyl Lithiation of N-Methylindoles 4.4 Regioselective Substitution of Methoxypyridinecarboxaldehydes 5. Conclusions