N-Alkylation Reactions and Indirect Formation of Amino Functionalities in Solid-Phase Synthesis

Christian A. Olsen; Henrik Franzyk; Jerzy W. Jaroszewski

doi:10.1055/s-2005-869961

REVIEW

N-Alkylation Reactions and Indirect Formation of Amino Functionalities in Solid-Phase Synthesis

Christian A. Olsen*, Henrik Franzyk, Jerzy W. Jaroszewski
Department of Medicinal Chemistry, The Danish University of Pharmaceutical Sciences, Universitetsparken 2, 2100 Copenhagen, Denmark
Fax: +4535306041; e-Mail: cao@dfuni.dk;

Abstract

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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.

1 Introduction
2 Reductive Methods
2.1 Reductive Amination
2.2 Reduction of Amides/Peptides
2.3 Primary Amines by Miscellaneous Reductions
3 S_N2 Alkylation and Michael Addition
3.1 Halogen Displacement
3.2 Sulfonate Displacement
3.3 Epoxide Opening and Michael Additions
4 Fukuyama Sulfonamide Alkylations
4.1 Mitsunobu Conditions
4.2 Alkyl Halides and Alkyl Sulfonates
5 Aza-Wittig and Staudinger Reactions
6 Palladium-Catalyzed and Other Aryl Aminations
7 Miscellaneous
8 Conclusions

Key words

amines - N-alkylation - reductive amination - borane reduction - solid-phase synthesis

Full Text

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