Synthesis of highly functionalised spiro-indoles by a halogen atom transfer radical cyclization

The halogen atom transfer radical cyclization (HATRC) has been evaluated on N-(indolylmethyl)trichloroacetamides under Cu(I)Cl catalysis using nitrogen containing ligands. The ring closure leads to the formation of 3,3-spiro-3H-indoles in moderate to good yields by a 5-exo-mechanism. Derivatives wit...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2005-10 (38), p.4827-4829
Main Authors: Stevens, Christian V, Van Meenen, Ellen, Eeckhout, Yves, Vanderhoydonck, Bart, Hooghe, Wim
Format: Article
Language:English
Subjects:
Copper - chemistry
Cyclization
Free Radicals - chemistry
Indoles - chemical synthesis
Indoles - chemistry
Ligands
Molecular Structure
Spiro Compounds - chemical synthesis
Spiro Compounds - chemistry
Stereoisomerism
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Summary:The halogen atom transfer radical cyclization (HATRC) has been evaluated on N-(indolylmethyl)trichloroacetamides under Cu(I)Cl catalysis using nitrogen containing ligands. The ring closure leads to the formation of 3,3-spiro-3H-indoles in moderate to good yields by a 5-exo-mechanism. Derivatives with an N-electron withdrawing substituent also lead to a 5-exo-trig and not to a 6-endo-trig cyclization.
ISSN:1359-7345
1364-548X
DOI:10.1039/b508424e