Fast ester cleavage of sterically hindered α- and β-aminoesters under non-aqueous conditions. Application to the kinetic resolution of aziridine esters

Tetrahedron Letters

Volumn 41, Issue 5, 2000, Pages 655-658

  Alezra, Valérie ^a   Bouchet, Céline ^a   Micouin, Laurent ^a   Bonin, Martine ^a   Husson, Henri Philippe ^a  

^a FACULTÉ DES SCIENCES PHARMACEUTIQUES ET BIOLOGIQUES   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AZIRIDINE DERIVATIVE; ESTER DERIVATIVE;

ARTICLE; CHELATION; CHEMICAL REACTION KINETICS; FRANCE; MOLECULAR INTERACTION; SYNTHESIS;

EID: 0034728119     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02157-7     Document Type: Article

References (11)

1. Alezra, V.; Bonin, M.; Micouin, L.; Husson, H.-P. Tetrahedron Lett., 2000, 41, 651.
2. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 2nd Ed; Wiley: New York, 1981.
3. Gassman, P. G.; Schenk, W. N. J. Org. Chem. 1977, 42, 918.
4. Unlike the Gassman standard procedure, no additional amount of water was needed to perform the reaction. We assume that moisture present in the solvent and in unsublimed potassium t-butoxide is enough to provide the KOH equivalent needed for the first step of the deprotection.
5. 2. The organic phases were combined, dried and evaporated to give ester 1 (2R) as an oil (75 mg, 50%). The aqueous phase was treated as described for compound 3 (see Ref. 5a) to give acid 1 (2S) as its potassium salt (67 mg, 48%). 1 (2R).
6. 2O, THF) of this compound required 24 h for completion.
7. (a) Chung, S.-K.; Kang, D.-H. Tetrahedron: Asymmetry 1997, 8, 3027.
8. (b) Reetz, M. T. Angew. Chem., Int. Ed. Engl. 1991, 30, 1531.
9. Gassman, P. G.; Hodgson, P. K. G.; Balchunis, R. J. J. Am. Chem. Soc. 1976, 98, 1275.
10. These compounds were prepared according to a reported procedure. (a) Harada, K.; Nakamura, I. J. Chem. Soc., Chem. Commun. 1978, 522.
11. (b) Häner, R.; Maetzke, T.; Seebach, D. Helv. Chim. Acta 1987, 70, 1676.