Chiral N-Fmoc-β-Amino Alkyl Isonitriles Derived from Amino Acids: First Synthesis and Application in 1-Substituted Tetrazole Synthesis

A novel class of optically active N-Fmoc-protected amino isonitriles has been described for the first time. Conversion of the carboxyl group of Fmoc-β-amino acids into an isocyano group has resulted in a new class of N-urethane-protected amino isonitriles. All the isonitriles have been isolated as s...

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Bibliographic Details
Published in:Journal of organic chemistry 2009-01, Vol.74 (1), p.153-157
Main Authors: Sureshbabu, Vommina V, Narendra, N, Nagendra, G
Format: Article
Language:English
Subjects:
Amino Acids - chemistry
Azides - chemistry
Chemistry
Cyclization
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Molecular Conformation
Nitriles - chemical synthesis
Nitriles - chemistry
Organic chemistry
Preparations and properties
Stereoisomerism
Tetrazoles - chemistry
Trimethylsilyl Compounds - chemistry
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Summary:A novel class of optically active N-Fmoc-protected amino isonitriles has been described for the first time. Conversion of the carboxyl group of Fmoc-β-amino acids into an isocyano group has resulted in a new class of N-urethane-protected amino isonitriles. All the isonitriles have been isolated as stable solids, purified, and completely characterized. A synthetic application of the obtained isonitriles has also been demonstrated through the synthesis of 1-substituted tetrazole analogues of amino acids via a 2 + 3 cycloaddition with trimethylsilyl azide.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo801527d