Carba-methylephedrine and carba-pseudo-methylephedrine as tools for probing the role of the nitrogen atom of chiral amino alcohols in asymmetric synthesis

Synlett

Volumn , Issue SPEC. ISS., 1999, Pages 960-962

  Cahard, Dominique ^a   Ferron, Laurent ^a   Plaquevent, Jean Christophe ^a  

^a UNIVERSITÉ DE ROUEN   (France)

Author keywords

Carba ephedrine; Chiral alkoxide; Enantioselective dehydrohalogenation; Ephedrine

Indexed keywords

AMINOALCOHOL; CARBA PSEUDO METHYLEPHEDRINE; CARBAMETHYLEPHEDRINE; EPHEDRINE DERIVATIVE; METHYLEPHEDRINE; NITROGEN; PSEUDOEPHEDRINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOMER; MOLECULAR DYNAMICS; REACTION ANALYSIS; SYNTHESIS;

EID: 0033016285     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-3092     Document Type: Article

References (13)

1. See for examples : Gawley, R.E.; Aube, J. Principles of Asymmetric Synthesis, Pergamon, Oxford 1996.
2. Vadecard, J.; Plaquevent, J-C.; Duhamel, L.; Duhamel, P. J. Chem. Soc., Chem. Commun., 1993, 116. Vadecard, J.; Plaquevent, J-C.; Duhamel, L.; Duhamel, P.; Toupet, L. J. Org. Chem. 1994, 59, 2285. Amadji, M.; Vadecard, J.; Plaquevent, J-C.; Duhamel, L.; Duhamel, P. J. Am. Chem. Soc., 1996, 118, 12483. Amadji, M.; Vadecard, J.; Cahard, D.; Duhamel, L.; Duhamel, P.; Plaquevent, J-C. J. Org. Chem., 1998, 63, 5541.
3. Vadecard, J.; Plaquevent, J-C.; Duhamel, L.; Duhamel, P. J. Chem. Soc., Chem. Commun., 1993, 116. Vadecard, J.; Plaquevent, J-C.; Duhamel, L.; Duhamel, P.; Toupet, L. J. Org. Chem. 1994, 59, 2285. Amadji, M.; Vadecard, J.; Plaquevent, J-C.; Duhamel, L.; Duhamel, P. J. Am. Chem. Soc., 1996, 118, 12483. Amadji, M.; Vadecard, J.; Cahard, D.; Duhamel, L.; Duhamel, P.; Plaquevent, J-C. J. Org. Chem., 1998, 63, 5541.
4. Vadecard, J.; Plaquevent, J-C.; Duhamel, L.; Duhamel, P. J. Chem. Soc., Chem. Commun., 1993, 116. Vadecard, J.; Plaquevent, J-C.; Duhamel, L.; Duhamel, P.; Toupet, L. J. Org. Chem. 1994, 59, 2285. Amadji, M.; Vadecard, J.; Plaquevent, J-C.; Duhamel, L.; Duhamel, P. J. Am. Chem. Soc., 1996, 118, 12483. Amadji, M.; Vadecard, J.; Cahard, D.; Duhamel, L.; Duhamel, P.; Plaquevent, J-C. J. Org. Chem., 1998, 63, 5541.
5. Vadecard, J.; Plaquevent, J-C.; Duhamel, L.; Duhamel, P. J. Chem. Soc., Chem. Commun., 1993, 116. Vadecard, J.; Plaquevent, J-C.; Duhamel, L.; Duhamel, P.; Toupet, L. J. Org. Chem. 1994, 59, 2285. Amadji, M.; Vadecard, J.; Plaquevent, J-C.; Duhamel, L.; Duhamel, P. J. Am. Chem. Soc., 1996, 118, 12483. Amadji, M.; Vadecard, J.; Cahard, D.; Duhamel, L.; Duhamel, P.; Plaquevent, J-C. J. Org. Chem., 1998, 63, 5541.
6. This trivial nomenclature is preferred to the systematic one to readily allow a direct comparison with the amino alcohol series.
7. The full details of the X-ray crystallographic data have been deposited at the Cambridge Crystallographic Data Centre (CCDC 113910).
8. Mitsunobu, O. Synthesis 1981, 1.
9. For related studies using chiral alkoxides as Brønsted bases, see: Jones, C.D.; Simpkins, N.S.; Giblin, G.M.P. Tetrahedron Lett. 1998, 39, 1023. Hodgson, D.M.; Gibbs, A.R. Tetrahedron Asymmetry, 1996, 7, 407. Kumamoto, T.; Aoki, S.; Nakajima, M.; Koga, K. Tetrahedron Asymmetry, 1994, 5, 1431. Milne, D.; Murphy, P.J. J. Chem. Soc., Chem. Commun., 1993, 884. Willems, J.G.H.; De Vries, J.G.; Nolte, R.J.M.; Zwanenburg, B. Tetrahedron Lett., 1995, 36, 3917.
10. For related studies using chiral alkoxides as Brønsted bases, see: Jones, C.D.; Simpkins, N.S.; Giblin, G.M.P. Tetrahedron Lett. 1998, 39, 1023. Hodgson, D.M.; Gibbs, A.R. Tetrahedron Asymmetry, 1996, 7, 407. Kumamoto, T.; Aoki, S.; Nakajima, M.; Koga, K. Tetrahedron Asymmetry, 1994, 5, 1431. Milne, D.; Murphy, P.J. J. Chem. Soc., Chem. Commun., 1993, 884. Willems, J.G.H.; De Vries, J.G.; Nolte, R.J.M.; Zwanenburg, B. Tetrahedron Lett., 1995, 36, 3917.
11. For related studies using chiral alkoxides as Brønsted bases, see: Jones, C.D.; Simpkins, N.S.; Giblin, G.M.P. Tetrahedron Lett. 1998, 39, 1023. Hodgson, D.M.; Gibbs, A.R. Tetrahedron Asymmetry, 1996, 7, 407. Kumamoto, T.; Aoki, S.; Nakajima, M.; Koga, K. Tetrahedron Asymmetry, 1994, 5, 1431. Milne, D.; Murphy, P.J. J. Chem. Soc., Chem. Commun., 1993, 884. Willems, J.G.H.; De Vries, J.G.; Nolte, R.J.M.; Zwanenburg, B. Tetrahedron Lett., 1995, 36, 3917.
12. For related studies using chiral alkoxides as Brønsted bases, see: Jones, C.D.; Simpkins, N.S.; Giblin, G.M.P. Tetrahedron Lett. 1998, 39, 1023. Hodgson, D.M.; Gibbs, A.R. Tetrahedron Asymmetry, 1996, 7, 407. Kumamoto, T.; Aoki, S.; Nakajima, M.; Koga, K. Tetrahedron Asymmetry, 1994, 5, 1431. Milne, D.; Murphy, P.J. J. Chem. Soc., Chem. Commun., 1993, 884. Willems, J.G.H.; De Vries, J.G.; Nolte, R.J.M.; Zwanenburg, B. Tetrahedron Lett., 1995, 36, 3917.
13. For related studies using chiral alkoxides as Brønsted bases, see: Jones, C.D.; Simpkins, N.S.; Giblin, G.M.P. Tetrahedron Lett. 1998, 39, 1023. Hodgson, D.M.; Gibbs, A.R. Tetrahedron Asymmetry, 1996, 7, 407. Kumamoto, T.; Aoki, S.; Nakajima, M.; Koga, K. Tetrahedron Asymmetry, 1994, 5, 1431. Milne, D.; Murphy, P.J. J. Chem. Soc., Chem. Commun., 1993, 884. Willems, J.G.H.; De Vries, J.G.; Nolte, R.J.M.; Zwanenburg, B. Tetrahedron Lett., 1995, 36, 3917.