Irreversible Oxy-2-azonia-Cope Rearrangements for the Synthesis of Functionalized Allyl [alpha]-Amino Acid Derivatives

Irreversible Oxy-2-azonia-Cope Rearrangements for the Synthesis of Functionalized Allyl [alpha]-Amino Acid Derivatives

A general method to synthesize functionalized allyl [alpha]-amino acid derivatives through an irreversible oxy-2-azonia-Cope rearrangement is reported. In the presence of AlCl3, the reaction of imino ethyl glyoxalates with various [beta],[gamma]-unsaturated ketones furnished the corresponding allyl...

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Veröffentlicht in:European journal of organic chemistry 2014-04, Vol.2014 (11), p.2379
Hauptverfasser: Mu, Wenbo, Zhou, Lijun, Zou, Yue, Wang, Quanrui, Goeke, Andreas
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Amino acids
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container_title European journal of organic chemistry
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creator Mu, Wenbo
Zhou, Lijun
Zou, Yue
Wang, Quanrui
Goeke, Andreas
description A general method to synthesize functionalized allyl [alpha]-amino acid derivatives through an irreversible oxy-2-azonia-Cope rearrangement is reported. In the presence of AlCl3, the reaction of imino ethyl glyoxalates with various [beta],[gamma]-unsaturated ketones furnished the corresponding allyl [alpha]-amino acid derivatives. The key to the success of this method is the amide bond formation, which makes the rearrangement irreversible. This reaction system constitutes a new strategy for the synthesis of unusual allyl glycine derivatives, which are valuable synthetic intermediates. An efficient and operationally simple three-component version of this reaction was also performed.
doi_str_mv 10.1002/ejoc.201301818
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title Irreversible Oxy-2-azonia-Cope Rearrangements for the Synthesis of Functionalized Allyl [alpha]-Amino Acid Derivatives
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