Diastereoselective synthesis of N-(α-aryl-α-haloacetyl) amino acid esters by acylation using 3-aryl-2,2-dicyanooxiranes

Synthesis

Volumn , Issue 8, 1999, Pages 1341-1344

  Roger, Florence ^a   Le Pironnec, Marie Gabrielle ^a   Guerro, Michel ^a   Gougeon, Patrick ^a   Gall, Philippe ^b   Le Grel, Philippe ^a   Baudy Floc'h, Michèle ^a  

^a UNIVERSITÉ DE RENNES 1   (France)

^b INSA DE RENNES   (France)

Author keywords

Chiral amino esters; Diastereoselective excess; Epoxides; Metalloenolate; N ( aryl haloacetyl) amino acid esters; Oxiranes; halo ketenes

Indexed keywords

2,2 DICYANOOXIRANE; AMINO ACID DERIVATIVE; EPOXIDE; ESTER DERIVATIVE; ETHYLENE OXIDE DERIVATIVE; HALOGENATED HYDROCARBON; KETENE DERIVATIVE; TRIETHYLAMINE; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CRYSTAL STRUCTURE; DIASTEREOISOMER; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032822005     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-3552     Document Type: Article

References (16)

1. Podlech, J.; Seebach, D. Angew. Chem. Int. Ed. Engl. 1995, 34, 471.
2. Marti, R.E.; Bleicher, K.H.; Bair, K.W. Tetrahedron Lett. 1997, 38, 6145.
3. Brady, W.T. Tetrahedron 1981, 17, 2949.
4. Durst, T.; Koh, K. Tetrahedron Lett. 1992, 45, 6799.
5. Maryanoff, C.A.; Sorgi, K.L.; Zientek, A.M. J. Org. Chem. 1994, 59, 237.
6. Le Grel, P.; Baudy-Floc'h, M.; Robert, R. Synthesis 1987, 306.
7. Florac, C.; Le Grel, P.; Baudy-Floc'h, M.; Robert, R. Synthesis 1991, 741.
8. Khamliche, L.; Robert, A. Tetrahedron 1988, 9, 2503.
9. Le Pironnec, M.G.; Guinamant, J.L.; Robert, R.; Baudy-Floc'h, M. Synthesis 1997, 229.
10. Cavicchioni, G. Tetrahedron Letters 1987, 28, 2427.
11. Cavicchioni, G.; D'Angeli, F.; Casolari, A.; Orlandini, P. Synthesis 1988, 947.
12. D'Angeli, F.; Marchetti, P.; Cavicchioni, G.; Catelani, G.; Kamrani Nejad, F. M. Tetrahedron Asymmetry 1990, 1, 155.
13. Garcia, M.J.; Azerad, R. Tetrahedron Asymmetry 1997, 8, 85.
14. Epoxides 1 were prepared in a two-step procedure: for the first one, a Knoevenagel-Cope condensation, see Gardner, P.D.; Brandon, R.L. J. Org. Chem. 1957 22, 1704.
15. Texier-Boullet, F.; Foucaud, A. Tetrahedron Lett. 1982, 23, 4927.
16. For the second step, a stereospecific epoxidation of alkene by sodium hypochlorite, see Baudy, M.; Robert, A.; Foucaud, A. J. Org. Chem. 1978, 43, 3732.