Warning: Undefined array key "mm" in /www/wwwroot/www.ai-bt.com/si.php on line 10 Deprecated: trim(): Passing null to parameter #1 ($string) of type string is deprecated in /www/wwwroot/www.ai-bt.com/si.php on line 10 A peptide-embedded trifluoromethyl ketone catalyst for enantioselective epoxidation.

Literature DB >> 22315978

A peptide-embedded trifluoromethyl ketone catalyst for enantioselective epoxidation.

Abstract

The development of peptide-based oxidation catalysts that use a transiently generated dioxirane as the chemically active species is reported. The active catalyst is a chiral trifluoromethyl ketone (Tfk) with a pendant carboxylic acid that can be readily incorporated into a peptide. These peptides were capable of epoxidizing alkenes in high yield (up to 89%) and enantiomeric ratios (er) ranging from 69.0:31.0 to 91.0:9.0, depending on the alkene substitution pattern.

Entities: Chemical

Mesh：

Substances：

Year: 2012 PMID： 22315978 PMCID： PMC3288446 DOI： 10.1021/ol3000712

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

14 in total

Review 1. The discovery of catalytically active peptides through combinatorial chemistry.

Authors: Albrecht Berkessel
Journal: Curr Opin Chem Biol Date: 2003-06 Impact factor: 8.822

2. In search of peptide-based catalysts for asymmetric organic synthesis.

Authors: Scott J Miller
Journal: Acc Chem Res Date: 2004-08 Impact factor: 22.384

3. Late-stage intermolecular CH activation for lead diversification: a highly chemoselective oxyfunctionalization of the C-9 position of potent bryostatin analogues.

Authors: Paul A Wender; Michael K Hilinski; Alexander V W Mayweg
Journal: Org Lett Date: 2005-01-06 Impact factor: 6.005

Review 4. Oligopeptides as catalysts for asymmetric epoxidation.

Authors: David R Kelly; Stanley M Roberts
Journal: Biopolymers Date: 2006 Impact factor: 2.505

5. A novel approach to the efficient oxygenation of hydrocarbons under mild conditions. Superior oxo transfer selectivity using dioxiranes.

Authors: Ruggero Curci; Lucia D'Accolti; Caterina Fusco
Journal: Acc Chem Res Date: 2006-01 Impact factor: 22.384

6. Aspartate-catalyzed asymmetric epoxidation reactions.

Authors: Gorka Peris; Charles E Jakobsche; Scott J Miller
Journal: J Am Chem Soc Date: 2007-06-26 Impact factor: 15.419

Review 7. Organocatalytic oxidation. Asymmetric epoxidation of olefins catalyzed by chiral ketones and iminium salts.

Authors: O Andrea Wong; Yian Shi
Journal: Chem Rev Date: 2008-07-01 Impact factor: 60.622

8. Asymmetric enone epoxidation by short solid-phase bound peptides: further evidence for catalyst helicity and catalytic activity of individual peptide strands.

Authors: Albrecht Berkessel; Burkhard Koch; Claudio Toniolo; Mario Rainaldi; Quirinus B Broxterman; Bernard Kaptein
Journal: Biopolymers Date: 2006 Impact factor: 2.505

9. Synthesis of phosphine containing amino acids: utilization of peptide synthesis in ligand design.

Authors: Anton Agarkov; Scott Greenfield; Dejian Xie; Robert Pawlick; Gale Starkey; Scott R Gilbertson
Journal: Biopolymers Date: 2006 Impact factor: 2.505

10. Iminium salt catalysts for asymmetric epoxidation: the first high enantioselectivities.

Authors: Philip C Bulman Page; Benjamin R Buckley; A John Blacker
Journal: Org Lett Date: 2004-05-13 Impact factor: 6.005

8 in total

1. Function-Oriented Investigations of a Peptide-Based Catalyst that Mediates Enantioselective Allylic Alcohol Epoxidation.

Authors: Nadia C Abascal; Phillip A Lichtor; Michael W Giuliano; Scott J Miller
Journal: Chem Sci Date: 2014-11-01 Impact factor: 9.825

A peptide-embedded trifluoromethyl ketone catalyst for enantioselective epoxidation.

Review 1. The discovery of catalytically active peptides through combinatorial chemistry.

2. In search of peptide-based catalysts for asymmetric organic synthesis.

3. Late-stage intermolecular CH activation for lead diversification: a highly chemoselective oxyfunctionalization of the C-9 position of potent bryostatin analogues.

Review 4. Oligopeptides as catalysts for asymmetric epoxidation.

5. A novel approach to the efficient oxygenation of hydrocarbons under mild conditions. Superior oxo transfer selectivity using dioxiranes.

6. Aspartate-catalyzed asymmetric epoxidation reactions.

Review 7. Organocatalytic oxidation. Asymmetric epoxidation of olefins catalyzed by chiral ketones and iminium salts.

8. Asymmetric enone epoxidation by short solid-phase bound peptides: further evidence for catalyst helicity and catalytic activity of individual peptide strands.

9. Synthesis of phosphine containing amino acids: utilization of peptide synthesis in ligand design.

10. Iminium salt catalysts for asymmetric epoxidation: the first high enantioselectivities.

1. Function-Oriented Investigations of a Peptide-Based Catalyst that Mediates Enantioselective Allylic Alcohol Epoxidation.

2. Synthesis and evaluation of phenylalanine-derived trifluoromethyl ketones for peptide-based oxidation catalysis.

Review 3. Asymmetric Catalysis Mediated by Synthetic Peptides, Version 2.0: Expansion of Scope and Mechanisms.

4. Enhanced reactivity in dioxirane C-H oxidations via strain release: a computational and experimental study.

5. Enantioselective synthesis of 3-arylquinazolin-4(3H)-ones via peptide-catalyzed atroposelective bromination.

6. Stereoselective peptide catalysis in complex environments - from river water to cell lysates.

7. Tungsten-catalyzed asymmetric epoxidation of allylic and homoallylic alcohols with hydrogen peroxide.

8. A Bottom Up Approach Towards Artificial Oxygenases by Combining Iron Coordination Complexes and Peptides.