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An Efficient synthesis of orthogonally protected trans ‐ and cis ‐4‐aminopipecolic acid
Author(s) -
Szatmári István,
Kiss Loránd,
Fülöp Ferenc
Publication year - 2006
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570430539
Subject(s) - chemistry , diastereomer , inversion (geology) , cis–trans isomerism , stereochemistry , carboxylate , paleontology , structural basin , biology
A straightforward synthesis of orthogonally N α / N γ ‐protected trans ‐ and cis ‐4‐aminopipecolic acid is reported, starting from methyl cis ‐4‐hydroxypiperidine‐2‐carboxylate. The two diastereomers were synthesized with the aid of C‐4 inversion (the trans isomer) or double C‐4 inversion (the cis isomer).