Stereospecific Synthesis of cis-2, 4-Pyrrolidinedicarboxylic Acid and cis-2, 5-Piperidinedicarboxylic Acid

Yasushi ARAKAWA; Mika YASUDA; Masafumi OHNISHI; Shigeyuki YOSHIFUJI

doi:10.1248/cpb.45.255

Yasushi ARAKAWA, Mika YASUDA, Masafumi OHNISHI, Shigeyuki YOSHIFUJI

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Keywords: stereospecific synthesis, Diels-Alder adduct, ruthenium tetroxide, cis-2, 4-pyrrolidinedicarboxylic acid, cis-2, 5-piperidinedicarboxylic acid, 2-azabicyclo[2.2.1]hept-5-en-3-one

JOURNAL FREE ACCESS

1997 Volume 45 Issue 2 Pages 255-259

DOI https://doi.org/10.1248/cpb.45.255

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Abstract

Lactams derived from hetero Diels-Alder adducts were stereospecifically converted into cis-2, 4-pyrrolidinedicarboxylic acid and cis-2, 5-piperidinedicarboxylic acid by ruthenium tetroxide oxidation. Optically active (2S, 4S)-(-)-2, 4-pyrrolidinedicarboxylic acid and (2R, 4R)-(+)-2, 4-pyrrolidinedicarboxylic acid were synthesized from (1S, 4R)-(+)-2-azabicyclo[2.2.1]hept-5-en-3-one and (1R, 4S)-(-)-2-azabicyclo[2.2.1]hept-5-en-3-one, respectively.

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