Functionalized cis- and trans-fused bicyclic alpha-amino acids via stereoselective double annulation and dequaternization reactions.
Fused bicyclic alpha-amino acids can be prepared by a double Michael reaction of p-anisyl ethynyl ketone and a tethered diacid, cyclization via hydrogenation or hydration of a CN group, and oxidation of the p-anisyl group. The substitution level of the alpha-amino acids can be adjusted by decyanation or decarboethoxylation of the intermediates. Bicyclic alpha-amino acids prepared in this way include cis- and trans-perhydroisoquinoline-3-carboxylic acids and cis-perhydro-2-pyrindine-3-carboxylic acids of various substitutions and oxidation levels. The bicyclic alpha-amino acids may be regarded as functionalized and conformationally restricted analogues of proline, pipecolic acid, 2-aminoadipic acid, or glutamic acid.
Hattori
Kazuyuki
K
Department of Chemistry, University of Kentucky, Lexington 40506-0055, USA.
Grossman
Robert B
RB
D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D006865:Hydrogenation; D007202:Indicators and Reagents; D013237:Stereoisomerism
D000596:Amino Acids; D019086:Bridged Bicyclo Compounds, Heterocyclic; D007202:Indicators and Reagents