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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Published inJournal of the American Chemical Society Vol. 137; no. 9; pp. 3225 - 3228
Main Authors Zi, Weiwei, Wu, Hongmiao, Toste, F. Dean
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 11.03.2015
Amer Chemical Soc
Subjects
Acetals - chemistry
Acetates - chemistry
Alkynes - chemistry
Catalysis
Chemistry
Chemistry Techniques, Synthetic
Chemistry, Multidisciplinary
Gold - chemistry
Indoles - chemistry
Ligands
Physical Sciences
Science & Technology
Stereoisomerism
CATALYZED CYCLOISOMERIZATION
GOLD
ASYMMETRIC ALLYLIC DEAROMATIZATION
IMINO-NAZAROV CYCLIZATION
CYCLOPROPANATION
ACETATES
ALKYNES
3+2 CYCLOADDITION
PROPARGYLIC CARBOXYLATES
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Summary: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.
Bibliography:NIH RePORTER
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ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.5b00613