Ruthenium porphyrin catalyzed intramolecular carbenoid C-H insertion. Stereloselective synthesis of cis-disubstituted oxygen and nitrogen heterocycles

[GRAPHIC] A ruthenium porphyrin-catalyzed stereoselective intramolecular carbenoid C-H insertion is described. Using [Ru-II(TTP)(CO)] as catalyst, aryl tosylhydrazones are converted to 2,3-dihydrobenzofurans, 2,3-dihydroindoles, and beta-lactams in good yields and remarkable cis selectivity (up to 99%). Enantioselective synthesis of 2,3-dihydrobenzofurans is also achieved with [Ru-II(D-4-Por*)(CO)] as catalyst, and up to 96% ee is attained.