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Methyl 2‐(Benzyloxycarbonylamino)‐2‐cyclopropylideneacetate: A Versatile Building Block for Cyclopropyl‐Containing Amino Acids
Author(s) -
Limbach Michael,
Lygin Alexander,
EsSayed Mazen,
de Meijere Armin
Publication year - 2009
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.200800817
Subject(s) - chemistry , nucleophile , octane , bicyclic molecule , yield (engineering) , michael reaction , peptidomimetic , block (permutation group theory) , amino acid , stereochemistry , combinatorial chemistry , organic chemistry , catalysis , peptide , biochemistry , materials science , metallurgy , geometry , mathematics
Methyl 2‐(benzyloxycarbonylamino)‐2‐cyclopropylideneacetate ( 2 ) was prepared in nine steps starting from L ‐serine in an overall yield of 24 %. It has been demonstrated to be reasonably reactive in Michael additions of various nucleophiles (6 examples, 75–98 % yields) as well as Diels–Alder reactions, both leading to new cyclopropyl‐containing amino acids in protected form. An application of 2 in the synthesis of methyl 4‐ tert ‐butoxycarbonylmethyl‐5‐oxo‐4,7‐diazaspiro[2.5]octane‐8‐carboxylate ( 15 ), a precursor for geometrically constrained bicyclic peptidomimetics of type 16 , has also been proved.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)