Alberto F. Garrido-Castro

@astrazeneca.com

Senior Scientist, Medicinal Chemistry, Early Oncology
AstraZeneca

Alberto F. Garrido-Castro


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https://researchid.co/agarrido
13

Scopus Publications

1074

Scholar Citations

13

Scholar h-index

13

Scholar i10-index

Scopus Publications

  • Total Synthesis of Dragocins A−C through Electrochemical Cyclization
    Brendyn P. Smith, Nathanyal J. Truax, Alexandros S. Pollatos, Michael Meanwell, Pranali Bedekar, et al.
    Angewandte Chemie International Edition, 2024
    The first total synthesis of dragocins A−C, remarkable natural products containing an unusual C4’ oxidized ribose architecture bridged by a polyhydroxylated pyrrolidine, is presented through a route featuring a number of uncommon maneuvers. Several generations towards the target molecules are presented, including the spectacular failure of a key C−H oxidation on a late‐stage intermediate. The final route features rapid, stereocontrolled access to a densely functionalized pyrrolidine and an unprecedented diastereoselective oxidative electrochemical cyclization to forge the hallmark 9‐membered ring. Preliminary studies suggest this electrochemical oxidation protocol is generally useful.
  • Scalable Electrochemical Decarboxylative Olefination Driven by Alternating Polarity**
    Alberto F. Garrido‐Castro, Yuta Hioki, Yoshifumi Kusumoto, Kyohei Hayashi, Jeremy Griffin, et al.
    Angewandte Chemie International Edition, 2023
    A mild, scalable (kg) metal‐free electrochemical decarboxylation of alkyl carboxylic acids to olefins is disclosed. Numerous applications are presented wherein this transformation can simplify alkene synthesis and provide alternative synthetic access to valuable olefins from simple carboxylic acid feedstocks. This robust method relies on alternating polarity to maintain the quality of the electrode surface and local pH, providing a deeper understanding of the Hofer‐Moest process with unprecedented chemoselectivity.
  • General electrochemical Minisci alkylation of N-heteroarenes with alkyl halides
    Roberto del Río-Rodríguez, Lorena Fragoso-Jarillo, Alberto F. Garrido-Castro, M. Carmen Maestro, Jose A. Fernández-Salas, et al.
    Chemical Science, 2022
    Herein, we report, a general, facile and environmentally friendly Minisci-type alkylation of N-heteroarenes under simple and straightforward electrochemical conditions using widely available alkyl halides as radical precursors.
  • α‐functionalization of imines via visible light photoredox catalysis
    Alberto F. Garrido-Castro, M. Carmen Maestro, José Alemán
    Catalysts, 2020
    The innate electrophilicity of imine building blocks has been exploited in organic synthetic chemistry for decades. Inspired by the resurgence in photocatalysis, imine reactivity has now been redesigned through the generation of unconventional and versatile radical intermediates under mild reaction conditions. While novel photocatalytic approaches have broadened the range and applicability of conventional radical additions to imine acceptors, the possibility to use these imines as latent nucleophiles via single-electron reduction has also been uncovered. Thus, multiple research programs have converged on this issue, delivering creative and practical strategies to achieve racemic and asymmetric α-functionalizations of imines under visible light photoredox catalysis.
  • Unlocking the direct photocatalytic difluoromethylation of CN bonds
    Alberto F. Garrido-Castro, Andrea Gini, M. Carmen Maestro, José Alemán
    Chemical Communications, 2020
    The current study presents a direct CF2H radical addition to CN bonds predicated on the photocatalytic activation of commercially available zinc difluoromethanesulfinate, achieving impressive structural diversity.
  • Intramolecular Homolytic Substitution Enabled by Photoredox Catalysis: Sulfur, Phosphorus, and Silicon Heterocycle Synthesis from Aryl Halides
    Alberto F. Garrido-Castro, Noelia Salaverri, M. Carmen Maestro, José Alemán
    Organic Letters, 2019
    Aryl radical generation and manipulation constitutes a long-standing challenge in organic synthesis. Photocatalytic single-electron reduction of aryl halides has been established as a premier activation pathway to reach these intermediates. The current study integrates the conceptual simplicity of the classical intramolecular homolytic substitution with the practicality of the modern photocatalytic approach. Predicated on an efficient metal-free dehalogenation of aryl halides under mild organo-photoredox conditions, sulfur, phosphorus, and silicon heteroatoms capture the C(sp2)-centered radical in an intramolecular fashion.
  • Electrochemically Driven, Ni-Catalyzed Aryl Amination: Scope, Mechanism, and Applications
    Yu Kawamata, Julien C. Vantourout, David P. Hickey, Peng Bai, Longrui Chen, et al.
    Journal of the American Chemical Society, 2019
    C-N cross-coupling is one of the most valuable and widespread transformations in organic synthesis. Largely dominated by Pd- and Cu-based catalytic systems, it has proven to be a staple transformation for those in both academia and industry. The current study presents the development and mechanistic understanding of an electrochemically driven, Ni-catalyzed method for achieving this reaction of high strategic importance. Through a series of electrochemical, computational, kinetic, and empirical experiments, the key mechanistic features of this reaction have been unraveled, leading to a second generation set of conditions that is applicable to a broad range of aryl halides and amine nucleophiles including complex examples on oligopeptides, medicinally relevant heterocycles, natural products, and sugars. Full disclosure of the current limitations and procedures for both batch and flow scale-ups (100 g) are also described.
  • A General Amino Acid Synthesis Enabled by Innate Radical Cross-Coupling
    Shengyang Ni, Alberto F. Garrido-Castro, Rohan R. Merchant, Justine N. de Gruyter, Daniel C. Schmitt, et al.
    Angewandte Chemie International Edition, 2018
    The direct union of primary, secondary, and tertiary carboxylic acids with a chiral glyoxylate-derived sulfinimine provides rapid access into a variety of enantiomerically pure α-amino acids (>85 examples). Characterized by operational simplicity, this radical-based reaction enables the modular assembly of exotic α-amino acids, including both unprecedented structures and those of established industrial value. The described method performs well in high-throughput library synthesis, and has already been implemented in three distinct medicinal chemistry campaigns.
  • Development and Application of Asymmetric Organocatalytic Mukaiyama and Vinylogous Mukaiyama-Type Reactions
    María Frías, Wioleta Cieślik, Alberto Fraile, Anielka Rosado-Abón, Alberto F. Garrido-Castro, et al.
    Chemistry A European Journal, 2018
    Organocatalysis is a growing area that is benefiting from advances in many fields. Its implementation has begun in areas such as supramolecular chemistry, organic chemistry and natural product synthesis. While a considerable number of important publications in the field of organocatalytic Mukaiyama-type additions have been reported, they are yet to be fully covered in a review. Therefore, we would like to highlight the applications of various kinds of organocatalysts in Mukaiyama-type reactions, while also including the vinylogous Mukaiyama variation. Herein we describe and discuss the development and current state of the art of the organocatalytic Mukaiyama reaction, vinylogous Mukaiyama and related reactions.
  • Asymmetric induction in photocatalysis – Discovering a new side to light-driven chemistry
    Alberto F. Garrido-Castro, M. Carmen Maestro, José Alemán
    Tetrahedron Letters, 2018
  • Intramolecular hydrogen-bond activation for the addition of nucleophilic imines: 2-hydroxybenzophenone as a chemical auxiliary
    Houcine Choubane, Alberto F. Garrido-Castro, Cuauhtemoc Alvarado, Ana Martín-Somer, Andrea Guerrero-Corella, et al.
    Chemical Communications, 2018
  • Asymmetric radical alkylation of: N -sulfinimines under visible light photocatalytic conditions
    Alberto F. Garrido-Castro, Houcine Choubane, Mortada Daaou, M. Carmen Maestro, José Alemán
    Chemical Communications, 2017
  • Multi-Ferrocene-Containing Silanols as Redox-Active Anion Receptors
    Sonia Bruña, Alberto F. Garrido-Castro, Josefina Perles, M. Merced Montero-Campillo, Otilia Mó, et al.
    Organometallics, 2016

RECENT SCHOLAR PUBLICATIONS

  • Total Synthesis of Dragocins A− C through Electrochemical Cyclization
    BP Smith, NJ Truax, AS Pollatos, M Meanwell, P Bedekar, ...
    Angewandte Chemie 136 (19), e202401107 , 2024
    2024
    Citations: 22
  • Total Synthesis of Dragocins A–C via Electrochemical Cyclization
    BP Smith, NJ Truax, AS Pollatos, M Meanwell, P Bedekar, ...
    Angewandte Chemie (International ed. in English) 63 (19), e202401107 , 2024
    2024
  • Scalable Electrochemical Decarboxylative Olefination Driven by Alternating Polarity
    AF Garrido‐Castro, Y Hioki, Y Kusumoto, K Hayashi, J Griffin, KC Harper, ...
    Angewandte Chemie International Edition 62 (42), e202309157 , 2023
    2023
    Citations: 70
  • General electrochemical Minisci alkylation of N-heteroarenes with alkyl halides
    R del Río-Rodríguez, L Fragoso-Jarillo, AF Garrido-Castro, MC Maestro, ...
    Chemical Science 13 (22), 6512-6518 , 2022
    2022
    Citations: 39
  • Photo-and Organo-Catalytic Strategies for the &Preparation of Nitrogen Compounds &
    AF Garrido Castro
    2021
  • α-Functionalization of imines via visible light photoredox catalysis
    AF Garrido-Castro, MC Maestro, J Aleman
    Catalysts 10 (5), 562 , 2020
    2020
    Citations: 75
  • Unlocking the direct photocatalytic difluoromethylation of C [double bond, length as m-dash] N bonds
    AF Garrido-Castro, A Gini, MC Maestro, J Alemán
    Chemical Communications 56 (26), 3769-3772 , 2020
    2020
    Citations: 57
  • Amine and heterocycle synthesis enabled by photoredox catalysis
    A Garrido-Castro, M Carmen Maestro, J Aleman
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY 258 , 2019
    2019
  • Intramolecular homolytic substitution enabled by photoredox catalysis: sulfur, phosphorus, and silicon heterocycle synthesis from aryl halides
    AF Garrido-Castro, N Salaverri, MC Maestro, J Aleman
    Organic Letters 21 (13), 5295-5300 , 2019
    2019
    Citations: 54
  • Electrochemically driven, Ni-catalyzed aryl amination: scope, mechanism, and applications
    Y Kawamata, JC Vantourout, DP Hickey, P Bai, L Chen, Q Hou, W Qiao, ...
    Journal of the American Chemical Society 141 (15), 6392-6402 , 2019
    2019
    Citations: 369
  • A General Amino Acid Synthesis Enabled by Innate Radical Cross‐Coupling
    S Ni, AF Garrido‐Castro, RR Merchant, JN de Gruyter, DC Schmitt, ...
    Angewandte Chemie International Edition 57 (44), 14560-14565 , 2018
    2018
    Citations: 162
  • Development and Application of Asymmetric Organocatalytic Mukaiyama and Vinylogous Mukaiyama‐Type Reactions
    M Frías, W Cieślik, A Fraile, A Rosado‐Abón, AF Garrido‐Castro, F Yuste, ...
    Chemistry–A European Journal 24 (43), 10906-10933 , 2018
    2018
    Citations: 54
  • Asymmetric induction in photocatalysis–Discovering a new side to light-driven chemistry
    AF Garrido-Castro, MC Maestro, J Aleman
    Tetrahedron Letters 59 (14), 1286-1294 , 2018
    2018
    Citations: 65
  • Intramolecular hydrogen-bond activation for the addition of nucleophilic imines: 2-hydroxybenzophenone as a chemical auxiliary
    H Choubane, AF Garrido-Castro, C Alvarado, A Martín-Somer, ...
    Chemical Communications 54 (27), 3399-3402 , 2018
    2018
    Citations: 13
  • Asymmetric radical alkylation of N-sulfinimines under visible light photocatalytic conditions
    AF Garrido-Castro, H Choubane, M Daaou, MC Maestro, J Alemán
    Chemical Communications 53 (55), 7764-7767 , 2017
    2017
    Citations: 76
  • Multi-Ferrocene-Containing Silanols as Redox-Active Anion Receptors
    S Bruña, AF Garrido-Castro, J Perles, MM Montero-Campillo, O Mó, ...
    Organometallics 35 (20), 3507-3519 , 2016
    2016
    Citations: 18

MOST CITED SCHOLAR PUBLICATIONS

  • Electrochemically driven, Ni-catalyzed aryl amination: scope, mechanism, and applications
    Y Kawamata, JC Vantourout, DP Hickey, P Bai, L Chen, Q Hou, W Qiao, ...
    Journal of the American Chemical Society 141 (15), 6392-6402 , 2019
    2019
    Citations: 369
  • A General Amino Acid Synthesis Enabled by Innate Radical Cross‐Coupling
    S Ni, AF Garrido‐Castro, RR Merchant, JN de Gruyter, DC Schmitt, ...
    Angewandte Chemie International Edition 57 (44), 14560-14565 , 2018
    2018
    Citations: 162
  • Asymmetric radical alkylation of N-sulfinimines under visible light photocatalytic conditions
    AF Garrido-Castro, H Choubane, M Daaou, MC Maestro, J Alemán
    Chemical Communications 53 (55), 7764-7767 , 2017
    2017
    Citations: 76
  • α-Functionalization of imines via visible light photoredox catalysis
    AF Garrido-Castro, MC Maestro, J Aleman
    Catalysts 10 (5), 562 , 2020
    2020
    Citations: 75
  • Scalable Electrochemical Decarboxylative Olefination Driven by Alternating Polarity
    AF Garrido‐Castro, Y Hioki, Y Kusumoto, K Hayashi, J Griffin, KC Harper, ...
    Angewandte Chemie International Edition 62 (42), e202309157 , 2023
    2023
    Citations: 70
  • Asymmetric induction in photocatalysis–Discovering a new side to light-driven chemistry
    AF Garrido-Castro, MC Maestro, J Aleman
    Tetrahedron Letters 59 (14), 1286-1294 , 2018
    2018
    Citations: 65
  • Unlocking the direct photocatalytic difluoromethylation of C [double bond, length as m-dash] N bonds
    AF Garrido-Castro, A Gini, MC Maestro, J Alemán
    Chemical Communications 56 (26), 3769-3772 , 2020
    2020
    Citations: 57
  • Intramolecular homolytic substitution enabled by photoredox catalysis: sulfur, phosphorus, and silicon heterocycle synthesis from aryl halides
    AF Garrido-Castro, N Salaverri, MC Maestro, J Aleman
    Organic Letters 21 (13), 5295-5300 , 2019
    2019
    Citations: 54
  • Development and Application of Asymmetric Organocatalytic Mukaiyama and Vinylogous Mukaiyama‐Type Reactions
    M Frías, W Cieślik, A Fraile, A Rosado‐Abón, AF Garrido‐Castro, F Yuste, ...
    Chemistry–A European Journal 24 (43), 10906-10933 , 2018
    2018
    Citations: 54
  • General electrochemical Minisci alkylation of N-heteroarenes with alkyl halides
    R del Río-Rodríguez, L Fragoso-Jarillo, AF Garrido-Castro, MC Maestro, ...
    Chemical Science 13 (22), 6512-6518 , 2022
    2022
    Citations: 39
  • Total Synthesis of Dragocins A− C through Electrochemical Cyclization
    BP Smith, NJ Truax, AS Pollatos, M Meanwell, P Bedekar, ...
    Angewandte Chemie 136 (19), e202401107 , 2024
    2024
    Citations: 22
  • Multi-Ferrocene-Containing Silanols as Redox-Active Anion Receptors
    S Bruña, AF Garrido-Castro, J Perles, MM Montero-Campillo, O Mó, ...
    Organometallics 35 (20), 3507-3519 , 2016
    2016
    Citations: 18
  • Intramolecular hydrogen-bond activation for the addition of nucleophilic imines: 2-hydroxybenzophenone as a chemical auxiliary
    H Choubane, AF Garrido-Castro, C Alvarado, A Martín-Somer, ...
    Chemical Communications 54 (27), 3399-3402 , 2018
    2018
    Citations: 13
  • Total Synthesis of Dragocins A–C via Electrochemical Cyclization
    BP Smith, NJ Truax, AS Pollatos, M Meanwell, P Bedekar, ...
    Angewandte Chemie (International ed. in English) 63 (19), e202401107 , 2024
    2024
  • Photo-and Organo-Catalytic Strategies for the &Preparation of Nitrogen Compounds &
    AF Garrido Castro
    2021
  • Amine and heterocycle synthesis enabled by photoredox catalysis
    A Garrido-Castro, M Carmen Maestro, J Aleman
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY 258 , 2019
    2019