Asymmetric C2−C3 Cyclopentannulation of the Indole Ring

Chiral nonracemic alkynyl(alkoxy)carbene complexes of tungsten(0) undergo the [3 + 2] cyclization toward α-methylindoles and 1,6-dimethyl-1,2,3,4-tetrahydropyridine to provide 2,3-indoline-fused cyclopentenone and 2,3-piperidine-fused cyclopentenone skeletons, respectively, with very high enantiomer...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2009-02, Vol.131 (6), p.2096-2097
Main Authors: Barluenga, José, Tudela, Eva, Ballesteros, Alfredo, Tomás, Miguel
Format: Article
Language:English
Subjects:
Alkynes - chemistry
Cyclopentanes - chemical synthesis
Indoles - chemical synthesis
Indoles - chemistry
Piperidines - chemical synthesis
Pyridines - chemistry
Stereoisomerism
Tungsten - chemistry
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Summary:Chiral nonracemic alkynyl(alkoxy)carbene complexes of tungsten(0) undergo the [3 + 2] cyclization toward α-methylindoles and 1,6-dimethyl-1,2,3,4-tetrahydropyridine to provide 2,3-indoline-fused cyclopentenone and 2,3-piperidine-fused cyclopentenone skeletons, respectively, with very high enantiomeric purities (96−99% ee).
ISSN:0002-7863
1520-5126
DOI:10.1021/ja809919t