Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

A Mild, Functional Group Tolerant Addition of Organozinc Nucleophiles to N-Activated Quinolines and Isoquinolines

A Mild, Functional Group Tolerant Addition of Organozinc Nucleophiles to N-Activated Quinolines and Isoquinolines
Neil A. Strotman, Jeanne Ho, Michael R. Luzung, Carlos A. Guerrero, Darryl D. Dixon, Martin D. Eastgate, Michael A. Schmidt, Sloan Ayers, Adrian Ortiz
An addition of organozinc nucleophiles to N-acyl activated quinolines and isoquinolines is described. Simple transmetalation with the corresponding Grignard reagents using ZnCl2 forms organozinc compounds which are functional group tolerant and stable to reactive acyl chloride reagents for extended periods. A wide variety of substrates which include reactive electron-withdrawing groups are well tolerated to form 2-substituted dihydroquinolines and dihydroisoquinolines. This methodology has been applied toward an improved synthetic route of uncialamycin and its analogs.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01882

DOI: 10.1021/acs.joc.7b01882

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