Irreversible Oxy‐2‐azonia‐Cope Rearrangements for the Synthesis of Functionalized Allyl α‐Amino Acid Derivatives1. Issue 11 (6th February 2014)

• Record Type: Journal Article
• Authors: Mu, Wenbo; Zhou, Lijun; Zou, Yue; Wang, Quanrui; Goeke, Andreas
• Is Part Of: European journal of organic chemistry. Issue 11(2014)
• Page Start: 2379
• Page End: 2385
• Publication Date: 2014-02-06
• Subjects: Amino acids -- Allylic compounds -- Sigmatropic rearrangement -- Lewis acids -- Multicomponent reactions; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201301818
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: 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 AlCl3, 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. Abstract : The oxy‐azonia‐Cope rearrangement of β, γ‐unsaturated ketones with imino ethyl glyoxalates was effectively promoted by Lewis acids to provide a preparatively useful approach to unusual allyl α‐amino acid derivatives. The key to the success of this method is the amide bond formation, which makes this transformation irreversible.