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Cover Picture: Synthesis of γ‐Oxo‐α,β‐dehydro‐α‐amino Acids from N – tert ‐Butyloxycarbonyl‐α‐Imino Esters and Carbonylmethyl 2‐Pyridinylsulfones via an Mannich‐Elimination Cascade (Asian J. Org. Chem. 7/2014)
Author(s) -
Wu Deyan,
Zhu Jin,
Sheng Chunquan,
Wang Wei,
Li Jian
Publication year - 2014
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Reports
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201490013
Subject(s) - chemistry , amino acid , peptide , metathesis , selectivity , combinatorial chemistry , organic chemistry , stereochemistry , catalysis , biochemistry , polymerization , polymer
The facile synthesis of γ‐oxo‐α,β‐dehydro‐α‐amino acids and α‐amino acids is described by Wei Wang and co‐workers in their Communication on page 766 ff. The process involves a Mannich‐elimination cascade process from N‐tert‐butyloxycarbonyl‐α‐imino esters with carbonylmethyl 2‐pyridinylsulfones. The γ‐oxo‐α,β‐dehydro‐α‐amino acids are produced in good yields with excellent E selectivity, and can easily be transformed into highly enantioenriched α‐amino acids via an asymmetric hydrogenation. Both classes of these amino‐acid derivatives have broad potential applications in organic synthesis and medicinal and peptide chemistry. Photo credit: Deyan Wu.