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Synthesis of Coumarins and Quinolones by Intramolecular Aldol Condensation Reactions of Titanium Enediolates

MPS-Authors
http://pubman.mpdl.mpg.de/cone/persons/resource/persons58380

Fürstner,  Alois
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

http://pubman.mpdl.mpg.de/cone/persons/resource/persons132877

Jumbam,  Denis N.
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

http://pubman.mpdl.mpg.de/cone/persons/resource/persons132886

Shi,  Nongyuan
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Fürstner, A., Jumbam, D. N., & Shi, N. (1995). Synthesis of Coumarins and Quinolones by Intramolecular Aldol Condensation Reactions of Titanium Enediolates. Zeitschrift für Naturforschung B, 50(3), 326-332.


Cite as: http://hdl.handle.net/11858/00-001M-0000-0014-A482-1
Abstract
Low-valent titanium prepared by the reduction of TiCl3 with zinc dust oxidatively adds to α-ketoamides or α-ketoesters with the formation of the corresponding titanium enediolates. These 1,2-difunctional nucleophiles, which have hardly been used in organic synthesis so far, undergo regioselective intramolecular aldol condensation reactions with various electrophiles such as aldehydes, ketones, nitriles, esters and amides. This methodology allows the synthesis of differently substituted coumarin and 2-quinolone derivatives.