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Synthesis of Unsaturated Amino Acids by [3,3]‐Sigmatropic Rearrangement of Chelate‐Bridged Glycine Ester Enolates
Author(s) -
Kazmaier Uli
Publication year - 1994
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199409981
Subject(s) - sigmatropic reaction , glycine , chemistry , yield (engineering) , amino acid , chelation , selectivity , metal , stereochemistry , medicinal chemistry , organic chemistry , catalysis , biochemistry , materials science , metallurgy
The highly diastereoselective formation of unsaturated α‐amino acids 2 by rearrangement of 1 has now been achieved under mild conditions and in very good yields by using metal enolates. The Ireland variant, which makes use of silylketene acetals, is hereby supplemented and in some cases the yield and selectivity are even improved. Z = benzyloxycarbonyl.