Ruthenium porphyrin catalyzed intramolecular carbenoid C[bond]H insertion. Stereoselective synthesis of cis-disubstituted oxygen and nitrogen heterocycles

Wai-Hung Cheung; Shi-Long Zheng; Wing-Yiu Yu; Guo-Chuan Zhou; Chi-Ming Che

doi:10.1021/ol034806q

Ruthenium porphyrin catalyzed intramolecular carbenoid C[bond]H insertion. Stereoselective synthesis of cis-disubstituted oxygen and nitrogen heterocycles

Org Lett. 2003 Jul 10;5(14):2535-8. doi: 10.1021/ol034806q.

Authors

Wai-Hung Cheung¹, Shi-Long Zheng, Wing-Yiu Yu, Guo-Chuan Zhou, Chi-Ming Che

Affiliation

¹ 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.

PMID: 12841774
DOI: 10.1021/ol034806q

Abstract

[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.