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 been used to construct a variety of substituted indoles that are not easily prepared by conventional indole annelation methods.
Original language | English (US) |
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Pages (from-to) | 4946-4947 |
Number of pages | 2 |
Journal | Journal of the American Chemical Society |
Volume | 128 |
Issue number | 15 |
DOIs | |
State | Published - Apr 19 2006 |
All Science Journal Classification (ASJC) codes
- Catalysis
- Chemistry(all)
- Biochemistry
- Colloid and Surface Chemistry