Optically active precursors for quaternary amino acids by addition of N- heteroaromatics to 3-alkylidene-2,5-diketopiperazines

Synlett

Volumn , Issue 4, 1999, Pages 459-461

  Jin, Shangde ^a   Liebscher, Jürgen ^a  

^a HUMBOLDT UNIVERSITY   (Germany)

Author keywords

3 Alkylidene diketopiperazines; Amino acids; Diketopiperazines; Isomerisation

Indexed keywords

AMINO ACID DERIVATIVE; DIOXANE; HETEROCYCLIC STEROID; PIPERAZINEDIONE;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; HYDROLYSIS; OPTICAL ROTATION; PRECURSOR; RACEMIC MIXTURE; STEREOCHEMISTRY;

EID: 0032895015     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2627     Document Type: Article

References (15)

1. Seebach, S.; Boes, M.; Naef, R.; Schweizer, W. B. J. Am. Chem. Soc. 1983, 105, 5390 and references cited therein.
2. Giannis, A.; Kolter, T. Angew. Chem. 1993, 105, 1303; Angew. Chem., Int. Ed. Engl. 1993, 32, 1244 and references cited therein.
3. Giannis, A.; Kolter, T. Angew. Chem. 1993, 105, 1303; Angew. Chem., Int. Ed. Engl. 1993, 32, 1244 and references cited therein.
4. Schöllkopf, U. Tetrahedron 1983, 39, 2085. Schöllkopf, U. Pure Appl. Chem. 1983, 55, 1799.
5. Schöllkopf, U. Tetrahedron 1983, 39, 2085. Schöllkopf, U. Pure Appl. Chem. 1983, 55, 1799.
6. Kawabata, T.; Wirth, T.; Yahiro, K.; Suzuki, H.; Fuji, K. J. Am. Chem. Soc. 1994, 116, 10809.
7. Hoffmann, M.; Seebach, D. Chimia, 1997, 51, 90.
8. Häusler, J.; Schmidt, U.; Chem. Ber. 1974, 107, 2804.
9. Poisel, H.; Schmidt, U. Chem. Ber. 1978, 106, 3408.
10. Machin, P. J.; Sammes, P. G. J. Chem. Soc., Perkin Trans, 1, 1974, 698.
11. Ottenheijm, H. C. J.; Plate, R.; Noordik, J. H.; Herscheid, D.M. J. Org. Chem. 1982, 47, 2147. Moyroud, J.; Gelin, J.; Chêne, A.; Mortier, J. Tetrahedron, 1996, 52, 8525.
12. Ottenheijm, H. C. J.; Plate, R.; Noordik, J. H.; Herscheid, D.M. J. Org. Chem. 1982, 47, 2147. Moyroud, J.; Gelin, J.; Chêne, A.; Mortier, J. Tetrahedron, 1996, 52, 8525.
13. 4 and evaporation under vacuum the remaining material was purified by column chromatography.
14. Marshall, J. A.; Schlaf, T. F.; Csernansky, J. G. Synth. Comm. 1975, 5, 237.
15. 2CH), 67.0 (C-proline), 112.7 (CH-indole), 115.1 (C-indole), 120.0 (CH-indole), 120.7 (CH-indole), 122.2 (CH-indole), 124.8 (CH-indole), 125.2 (C-indole), 127.8 (CH-phenyl), 129.2 (2CH-phenyl), 130.5 (2CH-phenyl), 137.0 (C-phenyl), 138.0 (C-indole), 164.7 (C=O), 168.4 (C=O).