Stereospecific synthesis of new 2,3,4,5-piperidinetetracarboxylic acids and 2,3,5-piperidinetricarboxylic acids

Tetrahedron

Volumn 59, Issue 38, 2003, Pages 7555-7563

  Arakawa, Yasushi ^a   Murakami, Tomoaki ^a   Ozawa, Fumiko ^a   Arakawa, Yukimi ^a   Yoshifuji, Shigeyuki ^a  

^a HOKURIKU UNIVERSITY   (Japan)

Author keywords

1,2 dihydropyridine; 2,3,4,5 piperidinetetracarboxylic acid; 2,3,5 piperidinetricarboxylic acid; Diels Alder adduct; Ruthenium tetroxide

Indexed keywords

1 (TERT BUTOXYCARBONYL) 3 (METHOXYCARBONYL) 2,5 PIPERIDINEDICARBOXYLIC ACID; 1 (TERT BUTOXYCARBONYL) 3,4 BIS(METHOXYCARBONYL) 2,5 PIPERIDINEDICARBOXYLIC ACID; 1 TERT BUTYL 2,3,5 TRIMETHYL 1,2,3,5 PIPERIDINETETRACARBOXYLATE; 1,2 DIHYDROPYRIDINE; 2 METHYL 6 (2 PHENOXYETHYL) 2 AZABICYCLO[2.2.2]OCT 7 ENE 2,6 DICARBOXYLATE; 2 TERT BUTYL 5,6 DIMETHYL 2 AZABICYCLO[2.2.2]OCT 7 ENE 2,5,6 TRICARBOXYLATE; 2 TERT BUTYL 6 METHYL 2 AZABICYCLO[2.2.2]OCT 7 ENE 2,6 DICARBOXYLATE; 2,3,4,5 PIPERIDINETETRACARBOXYLATE ACID; 2,3,5 PIPERIDINETRICARBOXYLIC ACID; 6 BENZYL 2 METHYL 2 AZABICYCLO[2.2.2]OCT 7 ENE 2,6 DICARBOXYLATE; ACRYLIC ACID DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; DIMETHYL 2 AZABICYCLO[2.2.2]OCT 7 ENE 2,6 DICARBOXYLATE; MALEIC ACID DERIVATIVE; PENTAMETHYL 1,2,3,4,5 PIPERIDINEPENTACARBOXYLATE; PYRIDINE DERIVATIVE; RUTHENIUM DERIVATIVE; TRIMETHYL 2 AZABICYCLO[2.2.2]OCT 7 ENE 2,5,6 TRICARBOXYLATE; UNCLASSIFIED DRUG;

ARTICLE; DIELS ALDER REACTION; OXIDATION; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOSPECIFICITY; SYNTHESIS;

BETULACEAE; ENTEROBACTERIA PHAGE T4;

EID: 0042330502     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(03)01200-6     Document Type: Article

References (12)

1. Arakawa Y., Yasuda M., Ohnishi M., Yoshifuji S. Chem. Pharm. Bull. 45:1997;255-259.
2. (a) Weinstein B., Lin L.C.C., Fowler F.W. J. Org. Chem. 45:1980;1657-1661
3. (b) Wender P.A., Schaus J.M., Torney D.C. Tetrahedron Lett. 20:1979;2485-2488
4. (c) Mariano P.S., Dunaway-Mariano D., Huesmann P.L. J. Org. Chem. 44:1979;124-133
5. (d) Sundberg R.J., Bloom J.D. J. Org. Chem. 46:1981;4836-4842
6. (e) Mehmandoust M., Marazano C., Singh R., Gillet B., Césario M., Fourrey J.-L., Das B.C. Tetrahedron Lett. 29:1988;4423-4426
7. (f) Marazano C., Yannic S., Genisson Y., Mehmandoust M., Das B.C. Tetrahedron Lett. 31:1990;1995-1998.
8. Arakawa Y., Murakami T., Arakawa Y., Yoshifuji S. Chem. Pharm. Bull. 51:2003;96-97.
9. Campbell M.M., Mahon M.F., Sainsbury M., Searle P.A., Davies G.M. Tetrahedron Lett. 32:1991;951-954.
10. Overman L.E., Taylor G.F., Houk K.N., Domelsmith L.N. J. Am. Chem. Soc. 100:1978;3182-3189.
11. The MOPAC AM1 method was performed on a personal computer using the program Chem 3D Pro (ver. 5.0); the coefficients (pz) of the HOMO of Moc-DHP were as follows: N(1), -0.4424, C(3), -0.4431, C(4), -0.2753, C(5), 0.4854, C(6), 0.3838. Those of the LUMO of methyl acrylate were as follows: O(1′), -0.3450, C(2′), 0.4259, C(3′), 0.4836, C(4′), -0.6601. The new bonds would form between C(3) and C(4′), and between C(6) and C(3′). As for the secondary orbital interaction, the sign of the coefficient at C(2′) coincides with that at C(5), but is opposed to that at N(1).
12. Some signals were split or broadened due to the rotamers or the conformers.