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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
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 - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201402051
Subject(s) - chemistry , triethylamine , amino acid , cascade , mannich reaction , selectivity , stereochemistry , combinatorial chemistry , organic chemistry , catalysis , biochemistry , chromatography
A method for facile synthesis of γ‐oxo‐α,β‐dehydro‐α‐amino acids has been developed. The process involves a triethylamine‐mediated Mannich‐elimination cascade process from N ‐ tert ‐butyloxycarbonyl (Boc)‐α‐imino esters with carbonylmethyl 2‐pyridinylsulfones. The γ‐oxo‐α,β‐dehydro‐α‐amino acids are produced in good yields of 51–98 % and with excellent E selectivity. The γ‐oxo‐α,β‐dehydro‐α‐amino acid derivatives can be conveniently transformed to highly enantioenriched α‐amino acids via an asymmetric hydrogenation.