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Synthesis 2009(12): 1941-1959
DOI: 10.1055/s-0029-1216839
DOI: 10.1055/s-0029-1216839
REVIEW
© Georg Thieme Verlag
Stuttgart ˙ New York
The Chemistry of Deprotonated α-Aminonitriles
Further Information
Received
9 March 2009
Publication Date:
29 May 2009 (online)
Publication History
Publication Date:
29 May 2009 (online)
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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