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Irreversible Oxy‐2‐azonia‐Cope Rearrangements for the Synthesis of Functionalized Allyl α‐Amino Acid Derivatives
Author(s) -
Mu Wenbo,
Zhou Lijun,
Zou Yue,
Wang Quanrui,
Goeke Andreas
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201301818
Subject(s) - chemistry , amide , amino acid , glycine , organic chemistry , combinatorial chemistry , medicinal chemistry , biochemistry
A general method to synthesize functionalized allyl α‐amino acid derivatives through an irreversible oxy‐2‐azonia‐Cope rearrangement is reported. In the presence of AlCl 3 , the reaction of imino ethyl glyoxalates with various β,γ‐unsaturated ketones furnished the corresponding allyl α‐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.