Dearomatizing Anionic Cyclization of Substituted N-Cumyl-N-benzyl- benzamides on Treatment with LDA:  Synthesis of Partially Saturated Substituted Isoindolones

Dearomatizing Anionic Cyclization of Substituted N-Cumyl-N-benzyl- benzamides on Treatment with LDA:  Synthesis of Partially Saturated Substituted Isoindolones

On treatment with LDA, substituted N-benzylbenzamides (including those bearing electron-withdrawing, electron-donating, or conjugating groups) become lithiated and cyclize to give, after aqueous quench, a range of partially saturated isoindolones as single regio- and stereoisomers. In general, the i...

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Veröffentlicht in:Organic letters 2000-12, Vol.2 (26), p.4229-4232
Hauptverfasser: Clayden, Jonathan, Menet, Christel J, Mansfield, Darren J
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Menet, Christel J
Mansfield, Darren J
description On treatment with LDA, substituted N-benzylbenzamides (including those bearing electron-withdrawing, electron-donating, or conjugating groups) become lithiated and cyclize to give, after aqueous quench, a range of partially saturated isoindolones as single regio- and stereoisomers. In general, the isoindolones resist rearomatization. Reaction of N-cumyl-N-benzylbenzamides leads to cyclized products which may be deprotected to give N-unsubstituted isoindolones.
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title Dearomatizing Anionic Cyclization of Substituted N-Cumyl-N-benzyl- benzamides on Treatment with LDA:  Synthesis of Partially Saturated Substituted Isoindolones
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