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

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  • Stereospecific Synthesis of cis 2 4 Pyr

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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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