Highly stereoselective synthesis of optically active oxazolinyl oxiranes from azaenolates of a chiral 2-chloromethyloxazoline

Tetrahedron Letters

Volumn 41, Issue 27, 2000, Pages 5295-5298

  Florio, Saverio ^a   Capriati, Vito ^a   Luisi, Renzo ^a  

^a CNR   (Italy)

Author keywords

Boron azaenolate; Chiral oxazolines; Chiral oxiranyl oxazolines; Titanium azaenolate

Indexed keywords

BORON DERIVATIVE; ETHYLENE OXIDE DERIVATIVE; HETEROCYCLIC COMPOUND; KETONE DERIVATIVE; OXAZOLINE DERIVATIVE; TITANIUM DERIVATIVE;

ARTICLE; CHEMICAL BINDING; CHIRALITY; DIASTEREOISOMER; LOW TEMPERATURE; OPTICAL ROTATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034235925     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00809-1     Document Type: Article

References (12)

1. Meyers, A. I. J. Heterocyclic. Chem. 1998, 35, 991-1002, and references cited therein.
2. (a) Metalation of few heterosubstituted alkyloxazolines has been reported: Annunziata, R.; Cinquini, M.; Gilardi, A. Synthesis 1983, 1016-1017.
3. (b) Le Bail, M.; Aitken, D. J.; Vergne, F.; Husson, H. P. J. Chem. Soc., Perkin Trans. 1 1997, 1681-1689.
4. (c) Meyers, A. I.; Knaus, G.; Kendall, P. M. Tetrahedron Lett. 1974, 39, 3495-3498.
5. Florio, S.; Capriati, V.; Luisi, R. Tetrahedron Lett. 1996, 37, 4781-4784.
6. Florio, S.; Troisi, L.; Capriati, V.; Ingrosso, G. Tetrahedron Lett. 1999, 40, 6101-6104.
7. Florio, S.; Capriati, V.; Luisi, R.; Abbotto, A.; Pippel, D. J. Eur. J. Org. Chem. 2000, submitted.
8. Florio, S.; Capriati, V.; Luisi, R.; Abbotto, A. Tetrahedron Lett. 1999, 40, 7421-7425.
9. Kamata, K.; Sato, H.; Takagi, E.; Agata, I.; Meyers, A. I. Heterocycles 1999, 51, 373-378.
10. (a) Breton, P.; Andrè-Barres, C.; Langlois, Y. Synth. Commun. 1992, 22, 2543-2554.
11. (b) Mintz, M. J.; Walling, C. Org. Synth., Collect. Vol. 5, 1973, 184-187.(c) Less conveniently compound 1 can be prepared from (1S,2S)-(+)-2-amino-3-methoxy-1-phenyl-1-propanol and the ethyl imidate of chloroacetonitrile. See: Meyers, A. I.; Knaus, G.; Kendall, P. M. Tetrahedron Lett. 1974, 39, 3495-3498.
12. (c) Less conveniently compound 1 can be prepared from (1S,2S)-(+)-2-amino-3-methoxy-1-phenyl-1-propanol and the ethyl imidate of chloroacetonitrile. See: Meyers, A. I.; Knaus, G.; Kendall, P. M. Tetrahedron Lett. 1974, 39, 3495-3498.