论文信息 - Synthesis of 2,6-disubstituted morpholines through regioselective oxiranes ring opening by tosylamide under PTC conditions

Synthesis of 2,6-disubstituted morpholines through regioselective oxiranes ring opening by tosylamide under PTC conditions

Abstract Symmetric and non-symmetric 2,6-disubstituted morpholines were synthesized through regioselective nucleophilic ring opening of oxiranes with tosylamide under solid–liquid phase transfer catalysis (SL-PTC) conditions followed by cyclization of the tosylamido diols thus obtained and final deprotection of the corresponding N-tosyl morpholines. The morpholines prepared are interesting building blocks in the synthesis of pharmaceuticals and agrochemicals.

[1] A. Papagni,et al. The first chiral racemic Fischer-type aminocarbene complex bearing a C2 symmetry amine: stereochemical characteristics and application to Michael addition reactions , 1995 .

[2] D. Albanese,et al. Synthesis of N-sulfonyl aziridines through regioselective opening of epoxides under solid-liquid PTC conditions , 1999 .

[3] G. L. Patourel. Chemistry of plant protection , 1996 .

[4] R. Wegler. Chemie der Pflanzenschutz- und Schädlingsbekämpfungsmittel , 1970, Anzeiger für Schädlingskunde und Pflanzenschutz.

[5] C. D. S. Tomlin,et al. The Pesticide Manual , 2003 .

[6] A. Myers,et al. Efficient, stereoselective synthesis of trans-2,5-disubstituted morpholines. , 2004, Organic letters.

[7] R. Perrone,et al. Synthesis and absolute configuration of substituted morpholines , 1980 .

[8] S. Hernestam. Reaction of 1,1′-iminobis-2-butanols with sulfuric acid , 1983 .

[9] K. B. Sharpless,et al. Catalytic asymmetric aminohydroxylation provides a short taxol side-chain synthesis. , 1996, Acta chemica Scandinavica.

[10] Rajesh Dave,et al. Facile route to 3,5-disubstituted morpholines: enantioselective synthesis of O-protected trans-3,5-bis(hydroxymethyl)morpholines. , 2004, Organic letters.