Asymmetric 1,3-dipolar reactions of 3-sulfinylfuran-2(5 H )-ones with 11 H -dibenzo[ b,e ]azepine 5-oxide. Synthesis of pyrroloazepines via isoxazoloazepines

Autor:	M. Rosario Martín, Alberto Fraile, Ana M. Martin Castro, J. Ignacio Andrés Gil, José L. García Ruano
Rok vydání:	2004
Předmět:	chemistry.chemical_compound Dipole chemistry Stereochemistry Organic Chemistry Drug Discovery Oxide Diastereomer Regioselectivity Azepine Biochemistry Adduct
Zdroj:	Tetrahedron Letters. 45:4653-4656
ISSN:	0040-4039
DOI:	10.1016/j.tetlet.2004.04.108
Popis:	The addition of morphanthridine N-oxide ( 1 ) to homochiral 3-p-tolylsulfinylfuran-2(5H)-ones ( 2a and 2b ) under mild conditions affords furoisoxazoloazepines ( 3a and 3b ) in high yields and with complete regioselectivity. The π-facial and endo-selectivities are also complete from 2a , which yields anti-3a -endo as the only diastereoisomer, whereas cycloreversion determines that the anti-3b -endo adduct can be almost exclusively isolated from 2b . Proper manipulation of the furoisoxazoloazepines allows the synthesis of the optically pure isoxazoloazepines and pyrroloazepines.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::239b79179d0baf8c649014f67840eeb7 https://doi.org/10.1016/j.tetlet.2004.04.108 Zobrazit plný text záznamu Full Text from ScienceDirect