Asymmetric synthesis; XXXVII: Synthesis of 2,6-disubstituted piperazines from chiral non-racemic lactams

Synthesis

Volumn , Issue 7, 1996, Pages 833-837

  Schanen, Vincent ^a   Cherrier, Marie Pierre ^a   De Melo, Sebastiào Jose ^a   Quirion, Jean Charles ^a   Husson, Henri Philippe ^a  

^a FACULTÉ DES SCIENCES PHARMACEUTIQUES ET BIOLOGIQUES   (France)

Author keywords

(R) ( ) phenylglycinol; 2,6 disubstituted piperazine; asymmetric synthesis; metalation of carbamate; amino acid

Indexed keywords

PIPERAZINE DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0029947932     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-4299     Document Type: Article

References (12)

1. For part XXXVI see: Lallemand, M.-C.; Chiadmi, M.; Tomas, A.; Kunesch, N.; Husson, H.-P. Tetrahedron Lett. 1995, 36, 2053.
2. Schanen, V.; Riche, C.; Chiaroni, A.; Quirion, J.-C.; Husson, H.-P. Tetrahedron Lett. 1994, 35, 2533.
3. Mickelson, J.W.; Jacobsen, E.J. Tetrahedron: Asymmetry 1995, 6, 19. Mickelson, J.W.; Belonga, K.L.; Jacobsen, E.J. J. Org. Chem. 1995, 60, 4177.
4. Mickelson, J.W.; Jacobsen, E.J. Tetrahedron: Asymmetry 1995, 6, 19. Mickelson, J.W.; Belonga, K.L.; Jacobsen, E.J. J. Org. Chem. 1995, 60, 4177.
5. Beak, P.; Zajdel, W.J., Reitz, D.B. Chem. Rev. 1984, 84, 471.
6. Duthaler, R.O. Tetrahedron 1994, 50, 1539.
7. Williams, R.M. Synthesis of Optically Active α-Amino Acids, Vol. 7 of Organic Chemistry Series; Baldwin, J.E.; Magnus, P.D. Eds.; Pergamon: Oxford, 1989.
8. For a recent example of asymmetric synthesis of 5-alkylpiper-azine-2-carboxylic acids see: Falorni, M.; Giacomelli, G.; Satta, M.; Cossu, S. Synthesis 1994, 391.
9. Beak, P.; Lee, W.K. J. Org. Chem. 1993, 58, 1109.
10. Beak, P.; Lee, W.K. J. Org. Chem. 1990, 55, 2578.
11. Vacca, J.P.; Dorsey, B.D.; Schleif, W.A.; Levin, R.B.; McDaniel, S.L.; Darke, P.L.; Zugay, J.; Quintero, J.C.; Blahy, O.M.; Sardana, V.V.; Schlabach, A.J.; Graham, P.I.; Condra, J.H.; Gotlib, L.; Holloway, M.K.; Lin, J.; Chen, I.-W.; Vastag, K.; Ostovic, D.; Anderson, P.S.; Emirli, E.A.; Huff, J.R. Proc. Natl. Acad. Sci. USA 1994, 91, 4096.
12. Rossen, K.; Weissman, S.A.; Sager, J.; Reamer, R.A.; Askin, D.; Volante, R.P.; Reider, P.J. Tetrahedron Lett. 1995, 36, 6419.