Skip to main content
U.S. Department of Energy
Office of Scientific and Technical Information

Radical Termination via β-Scission Enables Photoenzymatic Allylic Alkylation Using “Ene”-Reductases

Journal Article · · ACS Catalysis
 [1];  [1];  [2];  [2];  [2];  [2];  [1]
  1. Department of Chemistry, Princeton University, Princeton, New Jersey 08544, United States; Department of Chemistry and Chemical Biology, Cornell University, Ithaca, New York 14850, United States
  2. Department of Chemistry, Princeton University, Princeton, New Jersey 08544, United States

Not provided.

Research Organization:
Princeton Univ., NJ (United States)
Sponsoring Organization:
USDOE Office of Science (SC)
DOE Contract Number:
SC0019370
OSTI ID:
1978320
Journal Information:
ACS Catalysis, Vol. 12, Issue 15; ISSN 2155-5435
Publisher:
American Chemical Society (ACS)
Country of Publication:
United States
Language:
English

References (51)

Importance of Drug Enantiomers in Clinical Pharmacology journal October 1985
Escape from Flatland: Increasing Saturation as an Approach to Improving Clinical Success journal November 2009
Stereoselective radical reactions journal January 2003
Transition metal–catalyzed alkyl-alkyl bond formation: Another dimension in cross-coupling chemistry journal April 2017
Catalytic alkylation of unactivated C(sp3)–H bonds for C(sp3)–C(sp3) bond formation journal January 2019
Asymmetric Transition Metal-Catalyzed Allylic Alkylations journal January 1996
Asymmetric catalysis activated by visible light journal January 2015
Catalysis of Radical Reactions: A Radical Chemistry Perspective journal October 2015
Visible Light Photoredox Catalysis with Transition Metal Complexes: Applications in Organic Synthesis journal March 2013
Organic Photoredox Catalysis journal June 2016
Dual Catalysis Strategies in Photochemical Synthesis journal April 2016
The merger of transition metal and photocatalysis journal July 2017
Enantioselective Radical Processes journal August 2003
Progress in Enantioselective Radical Cyclizations journal January 2017
Merging Photoredox Catalysis with Organocatalysis: The Direct Asymmetric Alkylation of Aldehydes journal October 2008
A Dual-Catalysis Approach to Enantioselective [2 + 2] Photocycloadditions Using Visible Light journal April 2014
Asymmetric photoredox transition-metal catalysis activated by visible light journal November 2014
Enantioselective Photoredox Catalysis Enabled by Proton-Coupled Electron Transfer: Development of an Asymmetric Aza-Pinacol Cyclization journal November 2013
Enantioselective photochemistry through Lewis acid–catalyzed triplet energy transfer journal December 2016
Recent trends in biocatalysis journal January 2021
Extending the application of biocatalysis to meet the challenges of drug development journal November 2018
Biocatalytic Asymmetric Synthesis of Chiral Amines from Ketones Applied to Sitagliptin Manufacture journal June 2010
Building Bridges: Biocatalytic C–C-Bond Formation toward Multifunctional Products journal June 2016
Design and evolution of enzymes for non-natural chemistry journal October 2017
Artificial Metalloenzymes: Reaction Scope and Optimization Strategies journal May 2017
The fourth wave of biocatalysis is approaching journal November 2017
Asymmetric redox-neutral radical cyclization catalysed by flavin-dependent ‘ene’-reductases journal December 2019
Photoenzymatic Generation of Unstabilized Alkyl Radicals: An Asymmetric Reductive Cyclization journal August 2020
Photoenzymatic Synthesis of α-Tertiary Amines by Engineered Flavin-Dependent “Ene”-Reductases journal November 2021
Ene‐Reductase: A Multifaceted Biocatalyst in Organic Synthesis journal March 2022
Photoexcitation of flavoenzymes enables a stereoselective radical cyclization journal June 2019
Quaternary Charge-Transfer Complex Enables Photoenzymatic Intermolecular Hydroalkylation of Olefins journal December 2020
Photoenzymatic enantioselective intermolecular radical hydroalkylation journal June 2020
Transition metal-catalysed allylic functionalization reactions involving radicals journal January 2020
Tin-free radical cyclization reactions initiated by visible light photoredox catalysis journal January 2010
Direct and enantioselective  -allylation of ketones via singly occupied molecular orbital (SOMO) catalysis journal October 2010
The intramolecular asymmetric allylation of aldehydes via organo-SOMO catalysis: A novel approach to ring construction journal January 2011
Trifluoromethylation of Allylsilanes under Photoredox Catalysis journal March 2013
New Radical Allylation Reaction journal January 1996
Acyclic Stereocontrol in Radical Reactions. Diastereoselective Radical Addition/Allylation of N-Propenoyloxazolidinone journal January 1996
Atom-transfer addition and annulation reactions of iodomalonates journal November 1989
Structural and Chemical Properties of Silyl Radicals journal July 1995
Enantioselective Free Radical Allyl Transfers from Allylsilanes Promoted by Chiral Lewis Acids journal October 1997
Reductive radical-polar crossover: traditional electrophiles in modern radical reactions journal January 2019
Visible Light Assisted Radical‐Polar/Polar‐Radical Crossover Reactions in Organic Synthesis journal April 2021
Engineering a Non‐Natural Photoenzyme for Improved Photon Efficiency** journal December 2021
Light-mediated reduction of flavoproteins with flavins as catalysts journal January 1978
Ground-State Electron Transfer as an Initiation Mechanism for Biocatalytic C–C Bond Forming Reactions journal June 2021
Electrophilicity and Nucleophilicity Index for Radicals journal July 2007
Assessment of Nucleophilicity and Electrophilicity of Radicals, and of Polar and Enthalpy Effects on Radical Addition Reactions1 journal November 1998
Radical philicity and its role in selective organic transformations journal June 2021