Ruthenium porphyrin catalyzed intramolecular carbenoid C[bond]H insertion. Stereoselective synthesis of cis-disubstituted oxygen and nitrogen heterocycles.
[reaction: see text] A ruthenium porphyrin-catalyzed stereoselective intramolecular carbenoid C[bond]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.
Cheung
Wai-Hung
WH
Department of Chemistry and Open Laboratory of Chemical Biology of the Institute of Molecular Technology for Drug Discovery and Synthesis, The University of Hong Kong, Pokfulam Road, Hong Kong.
Zheng
Shi-Long
SL
Yu
Wing-Yiu
WY
Zhou
Guo-Chuan
GC
Che
Chi-Ming
CM