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Ruthenium-catalyzed cyclization of 3-en-1-ynyl imines with nucleophiles via tandem 5-exo-dig cyclization and nucleophilic addition
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Ruthenium-catalyzed cyclization of 3-en-1-ynyl imines with nucleophiles via tandem 5-exo-dig cyclization and nucleophilic addition

Hung-Chin Shen, Chia-Wen Li and Rai-Shung Liu
Tetrahedron Letters, Vol.45(50), pp.9245-9247
06/12/2004

Abstract

Cyclization Imines Nucleophile
Treatment of 3-en-1-ynyl imines with TpRuPPh 3 (CH 3 CN) 2 PF 6 catalyst (1 mol %) in DCE (50°C, 6 h) effected catalytic cyclization with suitable nucleophiles and gave functionalized pyrroles in good yields. The reaction mechanism is proposed to proceed via (2-pyrrolyl)carbenoid intermediates derived from 5-exo-dig cyclization. This catalytic reaction works well with various nucleophiles, including water, alcohols and anilines. © 2004 Elsevier Ltd. All rights reserved.

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