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DOI: 10.1055/s-0029-1219149
Ethyl Isocyanoacetate as a Useful Glycine Equivalent
Publication History
Publication Date:
14 January 2010 (online)
Abstract
In this account, we describe a useful synthetic approach to construct diverse constrained α,α-dialkylated amino acid derivatives using ethyl isocyanoacetate as a glycine equivalent. Various unusual amino acid derivatives, such as cyclophane-, benzocyclobutene-, and diene-containing systems, are reported here.
1 Introduction
2 Traditional Methods for the Synthesis of Cyclic α-Amino Acid Derivatives
2.1 Bucherer-Berg Method
2.2 Strecker Method
2.3 Schmidt Rearrangement Method
3 Glycine Equivalents
4 Preparation of Isocyanides
5 Preparation of Ethyl Isocyanoacetate
6 Synthesis of Cyclic Amino Acid Derivatives Using Various Carbon Electrophiles
7 Synthesis of Unusual Cyclophane-Based α-Amino Acid Derivatives
8 Synthesis of Bis-Armed Amino Acid Derivatives
9 Synthesis and Applications of Acyclic and Alicyclic Amino Acid Derivatives
10 Conclusion
Key words
glycine equivalents - amino acids - isocyanides - phase-transfer catalysis - cycloadditions - metathesis - Suzuki coupling
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