Enantioselective Michael-Type Friedel-Crafts Reactions of Indoles to Enones Catalyzed by a Chiral Camphor-Based Brønsted Acid

Chiral Brønsted acid, D‐camphorsulfonic acid, was found to be practical and efficient in the catalysis of the enantioselective Michael‐type Friedel–Crafts reactions of indoles with aromatic enones to afford the corresponding β‐indolyl ketones in excellent yields and moderate enantioselectivities. A...

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Bibliographic Details
Published inEuropean Journal of Organic Chemistry Vol. 2006; no. 23; pp. 5225 - 5227
Main Authors Zhou, Wei, Xu, Li-Wen, Li, Lyi, Yang, Lei, Xia, Chun-Gu
Format Book Review Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 01.12.2006
WILEY‐VCH Verlag
Wiley
Subjects
Asymmetry
Chemistry
Chemistry, Organic
Dual Activation
Enones
Friedel-Crafts Reaction
Indoles
Michael addition
Physical Sciences
Science & Technology
Michael addition
ALPHA,BETA-UNSATURATED KETONES
COMPLEXES
CARBONYL-COMPOUNDS
asymmetry
ALKYLATIONS
enones
dual activation
indoles
CHEMISTRY
RECENT PROGRESS
IONIC LIQUIDS
Friedel-Crafts reaction
NITROALKENES
CONJUGATE ADDITION
ALKALOIDS
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Summary:Chiral Brønsted acid, D‐camphorsulfonic acid, was found to be practical and efficient in the catalysis of the enantioselective Michael‐type Friedel–Crafts reactions of indoles with aromatic enones to afford the corresponding β‐indolyl ketones in excellent yields and moderate enantioselectivities. A surprising synergistic effect was discovered between BmimBr and D‐CSA which leads to active catalytic systems for the Friedel–Crafts reaction. The efficiency of these systems might result from the catalytic Lewis acid activation of the Brønsted acids. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
Bibliography:ark:/67375/WNG-8HHQNNZJ-8
istex:815AE596EEA2E3F294CB46AC97A291465DD109FE
ArticleID:EJOC200600646
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200600646