Gold(I)-Catalyzed Dearomative Rautenstrauch Rearrangement: Enantioselective Access to Cyclopenta[b]indoles

Gold(I)-Catalyzed Dearomative Rautenstrauch Rearrangement: Enantioselective Access to Cyclopenta[b]indoles

A highly enantioselective dearomative Rautenstrauch rearrangement catalyzed by cationic (S)-DTBM-Segphosgold­(I) is reported. This reaction provides a straightforward method to prepare enantioenriched cyclopenta­[b]­indoles. These studies show vast difference in enantioselectivity in the reactions o...

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Veröffentlicht in:Journal of the American Chemical Society 2015-03, Vol.137 (9), p.3225-3228
Hauptverfasser: Zi, Weiwei, Wu, Hongmiao, Toste, F. Dean
Format: Artikel
Sprache:eng
Schlagworte:
Acetals - chemistry
Acetates - chemistry
Alkynes - chemistry
Catalysis
Chemistry Techniques, Synthetic
Gold - chemistry
Indoles - chemistry
Ligands
Stereoisomerism
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Zusammenfassung:A highly enantioselective dearomative Rautenstrauch rearrangement catalyzed by cationic (S)-DTBM-Segphosgold­(I) is reported. This reaction provides a straightforward method to prepare enantioenriched cyclopenta­[b]­indoles. These studies show vast difference in enantioselectivity in the reactions of propargyl acetates and propargyl acetals in the chiral ligand-controlled Rautenstrauch reaction.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.5b00613