2,5-diketopiperazines, new chiral auxiliaries for asymmetric Diels-Alder reactions

Tetrahedron Letters

Volumn 38, Issue 22, 1997, Pages 3849-3852

  Le, Thuy X H ^a   Bussolari, Jacqueline C ^a   Murray, William V ^a  

^a R W JOHNSON PHARMACEUTICAL RES I   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PIPERAZINE DERIVATIVE; PIPERAZINEDIONE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; SYNTHESIS;

BETULACEAE;

EID: 0030914135     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00769-7     Document Type: Article

References (13)

1. Helmchen, G.; Karge, P.; Weetman, J. Modern Synthetic Methods; Springer: Berlin, 1986; Vol. 19.
2. Paquette, L. A. Asymmetric Synthesis; Academic: New York, 1984.
3. Oppolzer, W.; Chapius, C.; Bernardinelli, G. Tetrahedron Lett. 1984, 25, 5885.
4. Oppolzer, W. Angew. Chem. 1984, 96, 840.
5. Oppolzer, W.; Chapius, C.; Dupuis, D.; Guo, M. Helv. Chim. Acta. 1985, 68, 2100.
6. Oppolzer, W.; Wills, M.; Kelly, M. J.; Signer, M.; Blagg, J. Tetrahedron Lett. 1990, 31, 5015.
7. Oppolzer, W.; Rodriquez, I.; Starkemann, C.; Walther, E. Tetrahedron Lett. 1990, 31, 5019.
8. Evans, D. A.; Chapman, K. T.; Bisaha, J. J. Am. Chem. Soc. 1988, 110, 1238-1256.
9. Ott, H.; Frey, J.; Hofmann, A. Tetrahedron 1963, 19, 1675-1684.
10. D + 141 (c 0.5, EtOH).
11. Diastereomeric ratios for cleaved acid adducts (by NMR) were: endo-2-carboxybicyclo[2.2.1]hept-5-ene (5), 90:1; : endo-2-carboxybicyclo[2.2.2]oct-6-ene (6), 75:1; The acid adducts of 7 and 8 were derivatized with (S) -(-)-α-Methylbenzylamine. The diastereomeric ratios of the methylbenzylamide derivatives of the cleaved acid adduct of 7 was 23:1 and 8 was 100:0 each by chiral HPLC.
12. Evans, D. A.; Chapman, K. T.; Hung, D. T.; Kawaguchi, A. T. Angew. Chem. Int. Ed. Engl. 1987, 26, 1184-1186.
13. CAChe Scientific, Inc.; Beaverton, Oregon 97077.