Enantioselective Organocatalytic Intramolecular Ring-Closing Friedel−Crafts-Type Alkylation of Indoles

Li, Changfeng; Liu, Hiu; Liao, Jie; Cao, Yi-Ju; Liu, Xiaopeng; Xiao, Wen‐Jing

doi:10.1021/ol0703130

Cited by 127 publications

(23 citation statements)

References 18 publications

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“…When a, b-unsaturated ketones were exploited, a primary-secondary diamine 62 was able to catalyze the transformation with excellent results [73]. Xiao and co-workers have shown two successful examples of asymmetric intramolecular Friedel-Crafts reaction (Scheme 19) [74,75]. The intramolecular ringclosing Friedel-Crafts-type alkylation of indolyl a,b-unsaturated aldehydes provided an enantioselective synthesis of tetrahydropyrano [3,4-b]indoles (THPIs) and tetrahydro-b-carbolines (THBCs) in the presence of a MacMillan catalyst [74].…”

Section: Asymmetric Michael Addition Reactionsmentioning

confidence: 99%

“…Xiao and co-workers have shown two successful examples of asymmetric intramolecular Friedel-Crafts reaction (Scheme 19) [74,75]. The intramolecular ringclosing Friedel-Crafts-type alkylation of indolyl a,b-unsaturated aldehydes provided an enantioselective synthesis of tetrahydropyrano [3,4-b]indoles (THPIs) and tetrahydro-b-carbolines (THBCs) in the presence of a MacMillan catalyst [74]. The other intramolecular hydroarylations of w-aryloxy-and arylamino-tethered a,b-unsaturated aldehydes enabled a straightforward access to optically active functional chromans and tetrahydroquinolines [75].…”

Section: Asymmetric Michael Addition Reactionsmentioning

confidence: 99%

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Asymmetric Organocatalysis

Liu

Gong

2011

Asymmetric Catalysis From a Chinese Perspective

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Asymmetric organocatalysis has been receiving considerable attention in the last decade and thereby made tremendous advances. Chinese researchers have also intensified efforts to investigate asymmetric organocatalysis by using diverse types of disciplines, including enamine, iminium, Brønsted acid, carbene, and Lewis base catalysis. As a result, a large number of excellent catalysts and elegant protocols have come out from China. This article summarizes the most representative achievements in enantioselective organocatalysis from Chinese groups.

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Section: Asymmetric Michael Addition Reactionsmentioning

confidence: 99%

Section: Asymmetric Michael Addition Reactionsmentioning

confidence: 99%

Asymmetric Organocatalysis

Liu

Gong

2011

Asymmetric Catalysis From a Chinese Perspective

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“…However, in initial experiments we did not obtain satisfactory enantioselectivity, probably because of the low catalyst turnover. Based on our previous successful use of iminium catalysis in intramolecular Friedel–Crafts‐type alkylation,10a,e we decided to investigate an alternative strategy of chiral amine as the organocatalyst for the intramolecular hydroarylation.…”

Section: Resultsmentioning

confidence: 99%

Highly Efficient Route to Functionalized Tetrahydrocarbazoles Using a Tandem Cross‐Metathesis/Intramolecular‐Hydroarylation Sequence

Chen

et al. 2010

Chemistry An Asian Journal

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The scope of the novel ruthenium-catalyzed tandem cross-metathesis/intramolecular-hydroarylation sequence is described. This methodology offers a practical and efficient synthesis of structurally diverse and complex tetrahydrocarbazoles in good to excellent yields (up to 98%). Moreover, preliminary efforts towards the development of an enantioselective version of the current process by sequential catalysis with ruthenium complex and chiral amine are presented, with high yields and enantioselectivities (up to 88% yield and 91% ee).

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“…Likewise, the iminium ion mechanism resulted one of the most useful options to organocatalytic intramolecular ring-closing Friedel-Crafts alkylation of indolyl , -unsaturated aldehydes such as 184 (Scheme 29) [57].…”

Section: Intramolecular Cyclizationsmentioning

confidence: 99%

An Organocatalytic Approach to the Synthesis of Six-Membered Heterocycles

Gasperi¹,

Punzi²,

Migliorini³

et al. 2011

COC

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"""In the last few years, the new era of organocatalysis opened up an effective and efficient way to high yielding metal free, enantio- and diastereoselective reactions leading to six-membered heterocycles. This review provides an overview of the current achievements in the organocatalytic synthesis of these crucial building blocks. Ranging from hetero-Diels-Alder to cycloadditions, from one step cyclizations to cascade reactions, recent results offer new powerful tools to obtain six membered heterocycles with facile procedures in high yields and stereoselection, often leading to many new stereogenic centres in a single reaction. The total syntheses of natural products having heterocyclic ring formation as crucial stage, are also reported. When available, alternative supported organocatalysts have been examined""

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Enantioselective Organocatalytic Intramolecular Ring-Closing Friedel−Crafts-Type Alkylation of Indoles

Abstract: An enantioselective organocatalytic intramolecular ring-closing Friedel-Crafts-type alkylation of indolyl alpha,beta-unsaturated aldehydes has been developed. This powerful new strategy allows enantioselective access to THPIs and THBCs in a straightforward and atom-economical manner.

Cited by 127 publications

References 18 publications

Asymmetric Organocatalysis

Asymmetric Organocatalysis

Highly Efficient Route to Functionalized Tetrahydrocarbazoles Using a Tandem Cross‐Metathesis/Intramolecular‐Hydroarylation Sequence

An Organocatalytic Approach to the Synthesis of Six-Membered Heterocycles

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