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Literature DB >> 17315068

Organocatalytic enantioselective indole alkylations of alpha,beta-unsaturated ketones.

Wei Chen¹, Wei Du, Lei Yue, Rui Li, Yong Wu, Li-Sheng Ding, Ying-Chun Chen.

Abstract

The C3-selective enantioselective Michael-type Friedel-Crafts alkylations of indoles with nonchelating alpha,beta-unsaturated alkyl ketones, catalysed by a chiral primary amine derived from natural cinchonine, were investigated. The reactions, in the presence of 30 mol% catalyst, were smoothly conducted at 0 to -20 degrees C. Moderate to good ee (47-89%) has been achieved.

Entities: Chemical

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Year: 2007 PMID： 17315068 DOI： 10.1039/b616504d

Source DB: PubMed Journal: Org Biomol Chem ISSN： 1477-0520 Impact factor: 3.876

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Cited

5 in total

1. Asymmetric aza-Michael reactions of alpha,beta-unsaturated ketones with bifunctional organic catalysts.

Authors: Xiaojie Lu; Li Deng
Journal: Angew Chem Int Ed Engl Date: 2008 Impact factor: 15.336

2. Cinchona alkaloid catalyzed enantioselective amination of α,β-unsaturated ketones: an asymmetric approach to Δ²-pyrazolines.

Authors: Nathaniel R Campbell; Bingfeng Sun; Ravi P Singh; Li Deng
Journal: Adv Synth Catal Date: 2011-11-01 Impact factor: 5.837

Organocatalytic enantioselective indole alkylations of alpha,beta-unsaturated ketones.

1. Asymmetric aza-Michael reactions of alpha,beta-unsaturated ketones with bifunctional organic catalysts.

2. Cinchona alkaloid catalyzed enantioselective amination of α,β-unsaturated ketones: an asymmetric approach to Δ²-pyrazolines.

3. Enantioselective organocatalytic α-fluorination of cyclic ketones.

4. Synthesis of β-Heteroaryl Propionates via Trapping of Carbocations with π-Nucleophiles.

5. Asymmetric Friedel-Crafts alkylation of indole with chalcones catalyzed by chiral phosphoric acids.

Organocatalytic enantioselective indole alkylations of alpha,beta-unsaturated ketones.

1. Asymmetric aza-Michael reactions of alpha,beta-unsaturated ketones with bifunctional organic catalysts.

2. Cinchona alkaloid catalyzed enantioselective amination of α,β-unsaturated ketones: an asymmetric approach to Δ2-pyrazolines.

3. Enantioselective organocatalytic α-fluorination of cyclic ketones.

4. Synthesis of β-Heteroaryl Propionates via Trapping of Carbocations with π-Nucleophiles.

5. Asymmetric Friedel-Crafts alkylation of indole with chalcones catalyzed by chiral phosphoric acids.

2. Cinchona alkaloid catalyzed enantioselective amination of α,β-unsaturated ketones: an asymmetric approach to Δ²-pyrazolines.