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

Featherston, Aaron L.; Miller, Scott J.

doi:10.1016/j.bmc.2016.07.012

Title: Synthesis and evaluation of phenylalanine-derived trifluoromethyl ketones for peptide-based oxidation catalysis

Authors:: Featherston, Aaron L.; Miller, Scott J.

Publication Date:: Sat Oct 01 00:00:00 EDT 2016

Sponsoring Org.:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

OSTI Identifier:: 1398013

Grant/Contract Number:: AC02-05CH11231

Resource Type:: Publisher's Accepted Manuscript

Journal Name:: Bioorganic and Medicinal Chemistry

Additional Journal Information:: Journal Name: Bioorganic and Medicinal Chemistry Journal Volume: 24 Journal Issue: 20; Journal ID: ISSN 0968-0896

Publisher:: Elsevier

Country of Publication:: United Kingdom

Language:: English

Citation Formats


                    Featherston, Aaron L., and Miller, Scott J. Synthesis and evaluation of phenylalanine-derived trifluoromethyl ketones for peptide-based oxidation catalysis.  United Kingdom: N. p., 2016. 
Web.  doi:10.1016/j.bmc.2016.07.012.

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                    Featherston, Aaron L., & Miller, Scott J. Synthesis and evaluation of phenylalanine-derived trifluoromethyl ketones for peptide-based oxidation catalysis.  United Kingdom.  https://doi.org/10.1016/j.bmc.2016.07.012

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                    Featherston, Aaron L., and Miller, Scott J. Sat .  
"Synthesis and evaluation of phenylalanine-derived trifluoromethyl ketones for peptide-based oxidation catalysis".  United Kingdom.  https://doi.org/10.1016/j.bmc.2016.07.012.

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@article{osti_1398013,

  title        = {Synthesis and evaluation of phenylalanine-derived trifluoromethyl ketones for peptide-based oxidation catalysis},

  author       = {Featherston, Aaron L. and Miller, Scott J.},

  abstractNote = {},

  doi          = {10.1016/j.bmc.2016.07.012},

  journal      = {Bioorganic and Medicinal Chemistry},

  number       = 20,

  volume       = 24,

  place        = {United Kingdom},

  year         = {Sat Oct 01 00:00:00 EDT 2016},

  month        = {Sat Oct 01 00:00:00 EDT 2016}

}

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Facile Synthesis of TMS-Protected Trifluoromethylated Alcohols Using Trifluoromethyltrimethylsilane (TMSCF ₃ ) and Various Nucleophilic Catalysts in DMF
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Title: Synthesis and evaluation of phenylalanine-derived trifluoromethyl ketones for peptide-based oxidation catalysis

Citation Formats

Synthesis of Enantiopure Epoxides Through Biocatalytic Approaches journal, October 1997

If CH Bonds Could Talk: Selective CH Bond Oxidation journal, March 2011

Much Improved Conditions for the Negishi Cross-Coupling of Iodoalanine Derived Zinc Reagents with Aryl Halides journal, November 2009

Functional Analysis of an Aspartate-Based Epoxidation Catalyst with Amide-to-Alkene Peptidomimetic Catalyst Analogues journal, August 2008

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Facile Synthesis of TMS-Protected Trifluoromethylated Alcohols Using Trifluoromethyltrimethylsilane (TMSCF 3 ) and Various Nucleophilic Catalysts in DMF journal, September 2006

Advances in Homogeneous and Heterogeneous Catalytic Asymmetric Epoxidation journal, May 2005

Trifluoromethyl ketones: properties, preparation, and application journal, January 2013

Synthesis of N-(Tert-Butoxycarbonyl)-A-Iodoalanine Methyl Ester: A Useful Building Block in the Synthesis of Nonnatural A-Amino Acids Via Palladium Catalyzed Cross Coupling Reactions journal, January 2005

Highly efficient synthesis of aryl and heteroaryl trifluoromethyl ketones via o-iodobenzoic acid (IBX) journal, August 2013

Allylic 1,3-strain as a controlling factor in stereoselective transformations journal, December 1989

Development of the first and practical method for enantioselective synthesis of 10B-enriched p-borono-l-phenylalanine journal, August 2008

A Peptide-Embedded Trifluoromethyl Ketone Catalyst for Enantioselective Epoxidation journal, January 2012

Organocatalytic Asymmetric Epoxidation and Aziridination of Olefins and Their Synthetic Applications journal, May 2014

An N -Aryl-Substituted Oxazolidinone-Containing Ketone-Catalyzed Asymmetric Epoxidation with Hydrogen Peroxide as the Primary Oxidant journal, August 2007

Biocatalytic conversion of epoxides journal, August 2003

Asymmetric epoxidation using hydrogen peroxide (H2O2) as primary oxidant journal, December 1999

Transition-metal-catalyzed epoxidations journal, May 1989

Asymmetric Organocatalytic Epoxidations: Reactions, Scope, Mechanisms, and Applications journal, June 2014

An Efficient Catalytic Asymmetric Epoxidation Method journal, November 1997

A Rational Approach to Catalytic Enantioselective Enolate Alkylation Using a Structurally Rigidified and Defined Chiral Quaternary Ammonium Salt under Phase Transfer Conditions journal, December 1997

Trifluoromethylation of Nonenolizable Carbonyl Compounds with a Stable Piperazino Hemiaminal of Trifluoroacetaldehyde journal, April 2001

Organocatalytic Asymmetric Epoxidation of Olefins by Chiral Ketones journal, July 2004

Chemoselective Hydroxylation of Aliphatic sp 3 C–H Bonds Using a Ketone Catalyst and Aqueous H 2 O 2 journal, December 2014

Studies of folded peptide-based catalysts for asymmetric organic synthesis journal, January 2006

Synthesis of Enantiopure Epoxides Through Biocatalytic Approaches
journal, October 1997

If CH Bonds Could Talk: Selective CH Bond Oxidation
journal, March 2011

Much Improved Conditions for the Negishi Cross-Coupling of Iodoalanine Derived Zinc Reagents with Aryl Halides
journal, November 2009

Functional Analysis of an Aspartate-Based Epoxidation Catalyst with Amide-to-Alkene Peptidomimetic Catalyst Analogues
journal, August 2008

2,2,2-Trifluoroacetophenone: An Organocatalyst for an Environmentally Friendly Epoxidation of Alkenes
journal, April 2014

Facile Synthesis of TMS-Protected Trifluoromethylated Alcohols Using Trifluoromethyltrimethylsilane (TMSCF ₃ ) and Various Nucleophilic Catalysts in DMF
journal, September 2006

Advances in Homogeneous and Heterogeneous Catalytic Asymmetric Epoxidation
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Trifluoromethyl ketones: properties, preparation, and application
journal, January 2013

Synthesis of N-(Tert-Butoxycarbonyl)-A-Iodoalanine Methyl Ester: A Useful Building Block in the Synthesis of Nonnatural A-Amino Acids Via Palladium Catalyzed Cross Coupling Reactions
journal, January 2005

Highly efficient synthesis of aryl and heteroaryl trifluoromethyl ketones via o-iodobenzoic acid (IBX)
journal, August 2013

Allylic 1,3-strain as a controlling factor in stereoselective transformations
journal, December 1989

Development of the first and practical method for enantioselective synthesis of 10B-enriched p-borono-l-phenylalanine
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A Peptide-Embedded Trifluoromethyl Ketone Catalyst for Enantioselective Epoxidation
journal, January 2012

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journal, August 2007

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journal, December 1999

Transition-metal-catalyzed epoxidations
journal, May 1989

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journal, June 2014

An Efficient Catalytic Asymmetric Epoxidation Method
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