Alberto F. Garrido-Castro
@ethz.ch
Postdoctoral Fellow
ETH Zürich
Scopus Publications
Scholar Citations
Scholar h-index
Scholar i10-index
Scopus Publications
Brendyn P. Smith, Nathanyal J. Truax, Alexandros S. Pollatos, Michael Meanwell, Pranali Bedekar, Alberto F. Garrido‐Castro, and Phil S. Baran
Wiley
AbstractThe 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.
Alberto F. Garrido‐Castro, Yuta Hioki, Yoshifumi Kusumoto, Kyohei Hayashi, Jeremy Griffin, Kaid C. Harper, Yu Kawamata, and Phil S. Baran
Wiley
AbstractA 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.
Roberto del Río-Rodríguez, Lorena Fragoso-Jarillo, Alberto F. Garrido-Castro, M. Carmen Maestro, Jose A. Fernández-Salas, and José Alemán
Royal Society of Chemistry (RSC)
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.
Alberto F. Garrido-Castro, M. Carmen Maestro, and José Alemán
MDPI AG
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.
Alberto F. Garrido-Castro, Andrea Gini, M. Carmen Maestro, and José Alemán
Royal Society of Chemistry (RSC)
The current study presents a direct CF2H radical addition to CN bonds predicated on the photocatalytic activation of commercially available zinc difluoromethanesulfinate, achieving impressive structural diversity.
Alberto F. Garrido-Castro, Noelia Salaverri, M. Carmen Maestro, and José Alemán
American Chemical Society (ACS)
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.
Yu Kawamata, Julien C. Vantourout, David P. Hickey, Peng Bai, Longrui Chen, Qinglong Hou, Wenhua Qiao, Koushik Barman, Martin A. Edwards, Alberto F. Garrido-Castro,et al.
American Chemical Society (ACS)
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.
Shengyang Ni, Alberto F. Garrido-Castro, Rohan R. Merchant, Justine N. de Gruyter, Daniel C. Schmitt, James J. Mousseau, Gary M. Gallego, Shouliang Yang, Michael R. Collins, Jennifer X. Qiao,et al.
Wiley
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.
María Frías, Wioleta Cieślik, Alberto Fraile, Anielka Rosado-Abón, Alberto F. Garrido-Castro, Francisco Yuste, and José Alemán
Wiley
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.
Alberto F. Garrido-Castro, M. Carmen Maestro, and José Alemán
Elsevier BV
Houcine Choubane, Alberto F. Garrido-Castro, Cuauhtemoc Alvarado, Ana Martín-Somer, Andrea Guerrero-Corella, Mortada Daaou, Sergio Díaz-Tendero, M. Carmen Maestro, Alberto Fraile, and José Alemán
Royal Society of Chemistry (RSC)
The addition of nucleophilic imines, using 2-hydroxybenzophenone as a chemical auxiliary, is presented.
Alberto F. Garrido-Castro, Houcine Choubane, Mortada Daaou, M. Carmen Maestro, and José Alemán
Royal Society of Chemistry (RSC)
In this communication, a new photocatalytic strategy for the addition of alkyl-radical derivatives to N-sulfinimines with complete diastereoselectivity and moderate to good yields is presented.
Sonia Bruña, Alberto F. Garrido-Castro, Josefina Perles, M. Merced Montero-Campillo, Otilia Mó, Angel E. Kaifer, and Isabel Cuadrado
American Chemical Society (ACS)
The ability of diferrocenylsilanediol, Fc2Si(OH)2 (5), and 1,1,3,3-tetraferrocenyldisiloxane-1,3-diol, Fc2(HO)Si–O–Si(OH)Fc2 (6), to act as new electroactive anion receptors for either acetate or chloride anions has been investigated in solution, in the solid state, and in the gas phase. 1H NMR spectroscopic titrations with anions reveal that the binding interaction causes chemical-shift perturbations not only in the Si–OH hydrogen-bonding donor motif but also in the ferrocenyl protons of receptors 5 and 6. Square-wave voltammetric studies evidence that multiferrocenyl silanols 5 and 6 exhibit higher ability for electrochemical sensing of acetate than chloride, since the corresponding half-wave potentials (E1/2) for the successive ferrocene oxidations display a higher cathodic shift in the presence of such an anion. Furthermore, single-crystal X-ray diffraction analyses of the tetrabutylammonium salts of complexes [Fc2Si(OH)2·CH3COO]− (8), [Fc2Si(OH)2·Cl]− (9), [Fc2(HO)Si–O–Si(OH)Fc2·CH3COO]− (10), [{Fc2(...