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Synthesis 2005(16): 2631-2653
DOI: 10.1055/s-2005-869961
DOI: 10.1055/s-2005-869961
REVIEW
© Georg Thieme Verlag Stuttgart · New York
N-Alkylation Reactions and Indirect Formation of Amino Functionalities in Solid-Phase Synthesis
Further Information
Received
21 April 2005
Publication Date:
26 August 2005 (online)
Publication History
Publication Date:
26 August 2005 (online)
Abstract
Aliphatic and aromatic amino functionalities are present in a wide variety of natural products and drugs, as well as in synthetic small molecular probes with therapeutic and/or diagnostic potential in drug discovery. As solid-phase synthesis and combinatorial chemistry have emerged as important tools for generation of compound libraries, development of broad-scope and efficient chemistry for the introduction of various functional groups into resin-anchored substrates is highly important. Herein, we present a review of the literature concerning formation of the amino functionality on solid phase.
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1 Introduction
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2 Reductive Methods
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2.1 Reductive Amination
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2.2 Reduction of Amides/Peptides
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2.3 Primary Amines by Miscellaneous Reductions
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3 SN2 Alkylation and Michael Addition
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3.1 Halogen Displacement
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3.2 Sulfonate Displacement
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3.3 Epoxide Opening and Michael Additions
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4 Fukuyama Sulfonamide Alkylations
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4.1 Mitsunobu Conditions
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4.2 Alkyl Halides and Alkyl Sulfonates
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5 Aza-Wittig and Staudinger Reactions
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6 Palladium-Catalyzed and Other Aryl Aminations
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7 Miscellaneous
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8 Conclusions
Key words
amines - N-alkylation - reductive amination - borane reduction - solid-phase synthesis
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