Journal of the American Chemical Society

Synthesis of indoles via 6π-electrocyclic ring closures of trienecarbamates

TJ Greshock, RL Funk

Index: Greshock, Thomas J.; Funk, Raymond L. Journal of the American Chemical Society, 2006 , vol. 128, # 15 p. 4946 - 4947

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Citation Number: 52

Abstract

A new method for the preparation of indoles from readily available α-haloenones and α- (trialkylstannyl) enecarbamates is described. Following a Stille coupling, trienecarbamate 2 is electronically activated to undergo a facile 6π-electrocyclic ring closure and subsequent oxidation to afford protected aniline 4. Upon deprotection and reductive amination, acid 5 underwent clean cyclization to N-acetylindole 6 (Ac2O, NEt3, 130° C). This method has ...