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Literature DB >> 21992567

Enantioselective and regioselective indium(III)-catalyzed addition of pyrroles to isatins.

Elisa G Gutierrez¹, Casey J Wong, Aziza H Sahin, Annaliese K Franz.

Abstract

The indium(III)-catalyzed enantioselective and regioselective addition of pyrroles to isatins is described. The effects of metal and solvent on the reactivity and selectivity are compared and discussed, demonstrating that the indium(III)-indapybox complex provides the most effective catalyst. A case of divergent reactivity between pyrroles and indoles is presented.

Entities: Chemical Disease Gene

Mesh：

Substances：
Pyrroles
Indium
Isatin

Year: 2011 PMID： 21992567 PMCID： PMC3235954 DOI： 10.1021/ol202329s

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

18 in total

1. Structure-activity relationships of the oxindole growth hormone secretagogues.

Authors: Teruhisa Tokunaga; W Ewan Hume; Jun Nagamine; Tetsuya Kawamura; Mutsuo Taiji; Ryu Nagata
Journal: Bioorg Med Chem Lett Date: 2005-04-01 Impact factor: 2.823

2. InCl3-catalyzed allylic Friedel-Crafts reactions toward the stereocontrolled synthesis of 1,2,3,4-tetrahydroquinolines.

Authors: David S Giera; Christoph Schneider
Journal: Org Lett Date: 2010-11-05 Impact factor: 6.005

3. Catalytic enantioselective Henry reactions of isatins: application in the concise synthesis of (S)-(-)-spirobrassinin.

Authors: Lu Liu; Shilei Zhang; Fei Xue; Guangshun Lou; Haoyi Zhang; Shichao Ma; Wenhu Duan; Wei Wang
Journal: Chemistry Date: 2011-05-30 Impact factor: 5.236

4. Catalytic asymmetric synthesis of substituted 3-hydroxy-2-oxindoles.

Authors: Nadine V Hanhan; Aziza H Sahin; Toby W Chang; James C Fettinger; Annaliese K Franz
Journal: Angew Chem Int Ed Engl Date: 2010 Impact factor: 15.336

5. Paratunamides A-D, oxindole alkaloids from Cinnamodendron axillare.

Authors: Toshinori Kagata; Shizuka Saito; Hideyuki Shigemori; Ayumi Ohsaki; Haruaki Ishiyama; Takaaki Kubota; Jun'ichi Kobayashi
Journal: J Nat Prod Date: 2006-10 Impact factor: 4.050

6. Enantioselective Friedel-Crafts reaction of beta-trifluoromethylated acrylates with pyrroles and its application to the synthesis of trifluorinated heliotridane.

Authors: Yiyong Huang; Etsuko Tokunaga; Satoru Suzuki; Motoo Shiro; Norio Shibata
Journal: Org Lett Date: 2010-03-05 Impact factor: 6.005

7. Enantioselective Friedel-Crafts alkylations catalyzed by bis(oxazolinyl)pyridine-scandium(III) triflate complexes.

Authors: David A Evans; Keith R Fandrick; Hyun-Ji Song; Karl A Scheidt; Risheng Xu
Journal: J Am Chem Soc Date: 2007-07-21 Impact factor: 15.419

8. Highly enantioselective ketone-ene reactions of trifluoropyruvate: significant counterion effect of the In(III)-pybox complex.

Authors: Jun-Feng Zhao; Teguh-Budiono W Tjan; Boon-Hong Tan; Teck-Peng Loh
Journal: Org Lett Date: 2009-12-17 Impact factor: 6.005

Enantioselective and regioselective indium(III)-catalyzed addition of pyrroles to isatins.

1. Structure-activity relationships of the oxindole growth hormone secretagogues.

2. InCl3-catalyzed allylic Friedel-Crafts reactions toward the stereocontrolled synthesis of 1,2,3,4-tetrahydroquinolines.

3. Catalytic enantioselective Henry reactions of isatins: application in the concise synthesis of (S)-(-)-spirobrassinin.

4. Catalytic asymmetric synthesis of substituted 3-hydroxy-2-oxindoles.

5. Paratunamides A-D, oxindole alkaloids from Cinnamodendron axillare.

6. Enantioselective Friedel-Crafts reaction of beta-trifluoromethylated acrylates with pyrroles and its application to the synthesis of trifluorinated heliotridane.

7. Enantioselective Friedel-Crafts alkylations catalyzed by bis(oxazolinyl)pyridine-scandium(III) triflate complexes.

8. Highly enantioselective ketone-ene reactions of trifluoropyruvate: significant counterion effect of the In(III)-pybox complex.

9. Highly enantioselective carbonyl-ene reactions catalyzed by In(III)-PyBox complex.

10. Remarkably mild and efficient intramolecular Friedel-Crafts cyclization catalyzed by In(III).

1. Further Developments and Applications of Oxazoline-Containing Ligands in Asymmetric Catalysis.

2. Lewis Acid-Promoted Enantioselective Dearomative Spirocyclizations of Allenes.

Review 3. Isatin and its derivatives: a survey of recent syntheses, reactions, and applications.

4. Titanium(IV)-catalyzed stereoselective synthesis of spirooxindole-1-pyrrolines.

5. Lewis Acid-Catalyzed Enantioselective Friedel-Crafts Alkylation of Pyrrole in Water.