Organic letters

Ruthenium porphyrin catalyzed intramolecular carbenoid CH insertion. Stereoselective synthesis of cis-disubstituted oxygen and nitrogen heterocycles

WH Cheung, SL Zheng, WY Yu, GC Zhou…

Index: Cheung, Wai-Hung; Zheng, Shi-Long; Yu, Wing-Yiu; Zhou, Guo-Chuan; Che, Chi-Ming Organic Letters, 2003 , vol. 5, # 14 p. 2535 - 2538

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Citation Number: 79

Abstract

A ruthenium porphyrin-catalyzed stereoselective intramolecular carbenoid CH insertion is described. Using [RuII (TTP)(CO)] as catalyst, aryl tosylhydrazones are converted to 2, 3- dihydrobenzofurans, 2, 3-dihydroindoles, and β-lactams in good yields and remarkable cis selectivity (up to 99%). Enantioselective synthesis of 2, 3-dihydrobenzofurans is also achieved with [RuII (D4-Por*)(CO)] as catalyst, and up to 96% ee is attained.