TY - JOUR
T1 - Functionalized cis- and trans-fused bicyclic α-amino acids via stereoselective double annulation and dequaternization reactions
AU - Hattori, Kazuyuki
AU - Grossman, Robert B.
N1 - Copyright:
Copyright 2011 Elsevier B.V., All rights reserved.
PY - 2003/2/21
Y1 - 2003/2/21
N2 - Fused bicyclic α-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 α-amino acids can be adjusted by decyanation or decarboethoxylation of the intermediates. Bicyclic α-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 α-amino acids may be regarded as functionalized and conformationally restricted analogues of proline, pipecolic acid, 2-aminoadipic acid, or glutamic acid.
AB - Fused bicyclic α-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 α-amino acids can be adjusted by decyanation or decarboethoxylation of the intermediates. Bicyclic α-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 α-amino acids may be regarded as functionalized and conformationally restricted analogues of proline, pipecolic acid, 2-aminoadipic acid, or glutamic acid.
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U2 - 10.1021/jo026643+
DO - 10.1021/jo026643+
M3 - Article
C2 - 12585881
AN - SCOPUS:0037458985
SN - 0022-3263
VL - 68
SP - 1409
EP - 1417
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 4
ER -