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

…, M Yasuda, M Ohnishi, S YOSHIFUJI

Index: Arakawa, Yasushi; Yasuda, Mika; Ohnishi, Masafumi; Yoshifuji, Shigeyuki Chemical and Pharmaceutical Bulletin, 1997 , vol. 45, # 2 p. 255 - 259

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Citation Number: 15

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, ...