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Literature DB >> 17076493

Kinetic resolutions of indolines by a nonenzymatic acylation catalyst.

Abstract

The first method for the kinetic resolution of indolines through catalytic N-acylation is described. To improve the selectivity factor, new planar-chiral PPY-derived catalysts were synthesized, wherein the chiral environment was systematically modified. This work provides a rare example of a nonenzyme-based acylation catalyst for the kinetic resolution of amines.

Entities: Chemical

Mesh：

Substances：
Indoles
indoline

Year: 2006 PMID： 17076493 PMCID： PMC2569996 DOI： 10.1021/ja0657859

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

9 in total

Review 1. Enantioselective nucleophilic catalysis with "Planar-Chiral" heterocycles.

Authors: G C Fu
Journal: Acc Chem Res Date: 2000-06 Impact factor: 22.384

2. Planar-chiral pyridine N-oxides, a new family of asymmetric catalysts: exploiting an eta(5)-C(5)Ar(5) ligand to achieve high enantioselectivity.

Authors: B Tao; M M Lo; G C Fu
Journal: J Am Chem Soc Date: 2001-01-17 Impact factor: 15.419

3. Tuning the enantioselective N-acetylation of racemic amines: a spectacular salt effect.

Authors: Stellios Arseniyadis; Pithani V Subhash; Alain Valleix; Suju P Mathew; Donna G Blackmond; Alain Wagner; Charles Mioskowski
Journal: J Am Chem Soc Date: 2005-05-04 Impact factor: 15.419

4. Efficiency in nonenzymatic kinetic resolution.

Authors: Edwin Vedejs; Mara Jure
Journal: Angew Chem Int Ed Engl Date: 2005-06-27 Impact factor: 15.336

5. Kinetic resolution of 2-oxazolidinones via catalytic, enantioselective N-acylation.

Authors: Vladimir B Birman; Hui Jiang; Ximin Li; Lei Guo; Eric W Uffman
Journal: J Am Chem Soc Date: 2006-05-24 Impact factor: 15.419

6. Ruthenium-catalyzed asymmetric hydrogenation of N-boc-indoles.

Authors: Ryoichi Kuwano; Manabu Kashiwabara
Journal: Org Lett Date: 2006-06-08 Impact factor: 6.005

7. Palladium-catalyzed arylation of cyclopentadienes

Authors:
Journal: Chemistry Date: 2000-09-15 Impact factor: 5.236

8. Kinetic Resolution of Amines by a Nonenzymatic Acylation Catalyst We thank Michael M.-C. Lo, Dr. J. Craig Ruble, and Beata Tao for helpful discussions and preliminary studies, and we also thank Dr. George P. Luke (ARIAD Pharmaceuticals, Inc.) for providing the primary amine illustrated in entry 8 of Table 1. Support has been provided by Bristol-Myers Squibb, Merck, the National Institutes of Health (National Institute of General Medical Sciences, R01-GM57034), Novartis, Pfizer, and Pharmacia.

Authors: Shigeru Arai; Stéphane Bellemin-Laponnaz; Gregory C. Fu
Journal: Angew Chem Int Ed Engl Date: 2001-01-05 Impact factor: 15.336

9. Pd(II)-catalyzed enantioselective oxidative tandem cyclization reactions. Synthesis of indolines through C-N and C-C bond formation.

Authors: Kai-Tai Yip; Min Yang; Ka-Lun Law; Nian-Yong Zhu; Dan Yang
Journal: J Am Chem Soc Date: 2006-03-15 Impact factor: 15.419

9 in total

15 in total

Kinetic resolutions of indolines by a nonenzymatic acylation catalyst.

Review 1. Enantioselective nucleophilic catalysis with "Planar-Chiral" heterocycles.

2. Planar-chiral pyridine N-oxides, a new family of asymmetric catalysts: exploiting an eta(5)-C(5)Ar(5) ligand to achieve high enantioselectivity.

3. Tuning the enantioselective N-acetylation of racemic amines: a spectacular salt effect.

4. Efficiency in nonenzymatic kinetic resolution.

5. Kinetic resolution of 2-oxazolidinones via catalytic, enantioselective N-acylation.

6. Ruthenium-catalyzed asymmetric hydrogenation of N-boc-indoles.

7. Palladium-catalyzed arylation of cyclopentadienes

9. Pd(II)-catalyzed enantioselective oxidative tandem cyclization reactions. Synthesis of indolines through C-N and C-C bond formation.

1. Synthesis of indolines via a domino Cu-catalyzed amidation/cyclization reaction.

2. Peptide-catalyzed kinetic resolution of formamides and thioformamides as an entry to nonracemic amines.

3. Palladium Catalyzed Asymmetric Three-Component Coupling of Boronic Esters, Indoles, and Allylic Acetates.

4. Efficient synthesis of oxazoles by dirhodium(II)-catalyzed reactions of styryl diazoacetate with oximes.

5. Rhodium-catalyzed asymmetric intramolecular hydroamination of unactivated alkenes.

6. Chiral Indoline Synthesis Via Enantioselective Intramolecular Copper-Catalyzed Alkene Hydroamination.

7. Acyl transfer catalysis with 1,2,4-triazole anion.

Review 8. Asymmetric Catalysis Mediated by Synthetic Peptides, Version 2.0: Expansion of Scope and Mechanisms.

9. Direct, Enantioselective Synthesis of Pyrroloindolines and Indolines From Simple Indole Derivatives.

10. Stereoelectronic basis for the kinetic resolution of N-heterocycles with chiral acylating reagents.