Synthesis of 1,3-Oxazolidines and 1,3-Dioxolanes by Reaction of (2R, 3R)-3-Methylamino-3-phenyl-1,2-propanediol with Electrophiles

Synthetic Communications

Volumn 33, Issue 24, 2003, Pages 4347-4354

  Hajji, Chakib ^a   Zaballos García, Elena ^a   Sepúlveda Arques, José ^a  

^a UNIVERSITY OF VALENCIA   (Spain)

Author keywords

Chemoselectivity; Dioxolanes; Oxazolidines

Indexed keywords

1,3 DIOXOLANE DERIVATIVE; 3 METHYLAMINO 3 PHENYL 1,2 PROPANEDIOL; DICHLOROMETHANE; DIMETHOXYPROPANE; OXAZOLIDINE DERIVATIVE; PROPANE; PROPANEDIOL DERIVATIVE; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ISOMERIZATION; NUCLEAR OVERHAUSER EFFECT; REACTION ANALYSIS; ROOM TEMPERATURE; STEREOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS; TECHNIQUE; TEMPERATURE DEPENDENCE;

EID: 0346433987     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-120026865     Document Type: Article

References (8)

1. Lázár, L.A.; Lakatos, G.; Fúlop, F.; Bernáth, G.; Riddell, F.G. Equilibria of ring-chain tautomeric mixtures derived from 3-amino-1,2-propanediol and aromatic aldehydes. Tetrahedron 1997, 53, 1081-1088.
2. Hajji, C.; Testa, M.L.; Salud-Bea, R.; Zaballos-García, E.; Server-Carrió, J.; Sepúlveda-Arques, J. Reaction of 3-methylamino-1,2-diols with dihalomethanes. Synthesis of chiral 4-substituted 3-methyltetrahydro-1,3-oxazin-5-ols. Tetrahedron 2000, 56, 8173-8177.
3. Juliá, S.; Sala, P.; Mazo, J.; Sancho, M.; Ochoa, C.; Elguero, J. ; Fayet, J.P.; Vertut, M.C. N-Polyazolylmethanes. 1. Synthesis and NMR study of N,N′-diazolylmethanes. J. Heterocycl. Chem. 1982, 19, 1141-1145.
4. Mills, J.A. The stereochemistry of cyclic derivatives of carbohydrates. Adv. Carbohydr. Chem. 1955, 10, 1-53;
5. (b) Capon, B. Mechanism in carbohydrate chemistry. Chem. Rev. 1969, 69, 407;
6. (c) Buchanan, J.G.; Moorhouse, S.J.; Wightman, R.H. C-nucleoside studies. 12. Synthesis of 3-alpha- and 3-beta-(D-xylofuranosyl)pyrazoles. J. Chem. Soc., Perkin. Trans. I 1981, 2258-2266.
7. El Ashry, E.S.H.; Rashed, N.; Mousaad, A.; El Habrouk, M. Isopropylidenation of aldosulose bis(phenylhydrazones). Carbohydr. Res. 1995, 269, 349-354;
8. (b) El Ashry, E.S.H.; El Kilany, Y.; Singab, F. Heterocycles from carbohydrate precursors. Part. 40. Kinetic and thermodynamic products of ketalation of 1-C-substituted L-threo-glycerol: a regioselective formation of 1,3-dioxolanes. J. Chem. Soc. Perkin. Trans. I 1988, 133-137.