The Chemistry of Deprotonated α-Aminonitriles

Till Opatz

doi:10.1055/s-0029-1216839

REVIEW

The Chemistry of Deprotonated α-Aminonitriles

Till Opatz*
Institut für Organische Chemie, Universität Hamburg, Martin-Luther-King-Platz 6, 20146 Hamburg, Germany
Fax: +49(40)428383834; e-Mail: opatz@chemie.uni-hamburg.de;

Abstract

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Abstract

This review highlights various aspects of the chemistry of the anions of α-aminonitriles. Their structural features and their characteristic reactivity are discussed, along with various methods for their preparation. Special emphasis is given to synthetic applications of deprotonated α-aminonitriles which have been used as valuable and readily accessible synthetic equivalents of acyl anions and α-aminocarbanions.

1 Introduction

2 Structure and Reactivity of Deprotonated α-Aminonitriles

3 Alkylations

4 Opening of Epoxides

5 1,2-Additions

6 Acylations

7 1,4-Additions

8 Reactions of Unsaturated α-Aminonitriles

9 Other Reactions

10 Deprotonation of N-Monosubstituted and N-Unsubstituted α-Aminonitriles

11 Deprotonated α-Aminonitriles in Asymmetric Synthesis

12 Conclusions

Key words

aminonitriles - carbanions - asymmetric synthesis - amines - ketones

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Referenzen

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