Journal: Organic Letters

Abbreviation

Org. Lett.

Publisher

American Chemical Society

Journal Volumes

ISSN

1523-7060
1523-7052

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Publications 1 - 10 of 188
  • Synthesis of Primary Amines via Hydrogen Atom Transfer-Initiated Cyclization/Reduction Cascade of Unsaturated Nitriles
    Item type: Journal Article
    Lindner, Henry; Schneider, Michael; Mader, Philipp; et al. (2024)
    Organic Letters
    We report a hydrogen atom transfer-initiated cyclization/reduction cascade for the synthesis of primary amines from delta,epsilon- and epsilon,zeta-unsaturated nitriles. The HAT transformation employs Mn(acac)3 as a catalyst and utilizes air as an oxidant along with NaBH4 as a dual-purpose reductant toward the olefin and subsequently C=N. Aromatic and aliphatic nitriles incorporating mono-, di-, and trisubstituted olefins are substrates for the reaction. Starting materials bearing malonates are transformed into the corresponding bicyclic lactams, enabling the rapid buildup of structural complexity.
  • An Efficient Synthesis Strategy to the Core Structure of 6-5-6-5-6-Membered Epipolythiodiketopiperazines
    Item type: Journal Article
    Zipfel, Hannes F.; Carreira, Erick M. (2014)
    Organic Letters
  • Enantioselective Conjugate Addition of Aldehydes to Oxetane- and Azetidine-Containing Nitroolefins: An Entry to Spirocyclic Pyrrolidines
    Item type: Journal Article
    Budinská, Alena; Lefebvre, Quentin; Wennemers, Helma (2025)
    Organic Letters
    Enantioselective amine-catalyzed conjugate additions of aldehydes to oxetane- and azetidine-containing nitroolefins afford γ-nitroaldehydes as key building blocks en route to spirocyclic oxetane/azetidine-pyrrolidines. The study provided insights into the stability and reactivity of these β,β-disubstituted nitroolefins and enabled the enantioselective synthesis of chiral oxetanes and azetidines in moderate-to-high yields and enantioselectivities. This approach expands synthetic access to medicinally relevant scaffolds and broadens the scope of enantioselective organocatalytic transformations.
  • Facile Formation of N-Acyl-oxazolidinone Derivatives Using Acid Fluorides
    Item type: Journal Article
    Schindler, Corinna S.; Forster, Patrik M.; Carreira, Erick M. (2010)
    Organic Letters
  • A modular approach to polyketide building blocks
    Item type: Journal Article
    Lohse-Fraefel, Nina; Carreira, Erick M. (2005)
    Organic Letters
  • Intermolecular Synthesis of Coumarins from Acid Chlorides and Unactivated Alkynes through Palladium Catalysis
    Item type: Journal Article
    Schmitt, Hendrik L.; Staeck, Niels; Müller, Patrick; et al. (2025)
    Organic Letters
    We describe a modular synthetic pathway to directly obtain coumarins from acid chlorides and alkynes. A Pd catalyst employing 3,5-CF₃-Ph-DPEPhos as the ancillary ligand was found to unlock this reactivity, enabling the conversion of a variety of 2-methoxy benzoyl chlorides and alkynes to the corresponding coumarins. Besides acid chlorides, the in situ generation of this reactive species from the corresponding acid was also possible. Finally, control experiments and preliminary kinetic analyses were performed to understand the role of the catalyst.
  • Evaluating Participation Modes in Peracetylated Glycosyl Cations
    Item type: Journal Article
    Geue, Niklas; Greis, Kim; Omoregbee-Leichnitz, Sabrina; et al. (2026)
    Organic Letters
    Neighboring group participation and remote participation are fundamental concepts in carbohydrate chemistry and are commonly applied to achieve stereocontrol in glycosylation reactions. The corresponding intermediates can be glycosyl cations, which are challenging to characterize due to their short-lived nature. Using gas-phase infrared spectroscopy supported by density functional theory calculations, we directly assess and rank the participation modes of acetyl protecting groups in peracetylated glucosyl, galactosyl, and mannosyl cations, showing that neighboring group participation and hence the formation of C2-dioxolenium ions is found experimentally in all three cases. Energetic ranking of theoretical structures in vacuo revealed differences in the remote participation preferences depending on the hexose, showing that C3-dioxolenium ions are preferred for glucose and particularly mannose, whereas C4-dioxolenium ions are most stable in the case of galactose. These findings contribute to our fundamental understanding of protecting group participation and could facilitate glycosylation strategies in the future.
  • Solid-Phase Synthesis of Photochromic Spiropyrans
    Item type: Journal Article
    Zhao, Weili; Carreira, Erick M. (2005)
    Organic Letters
  • Enantioselective Iridium-Catalyzed α-Allylation with Aqueous Solutions of Acetaldehyde
    Item type: Journal Article
    Sandmeier, Tobias; Carreira, Erick M. (2020)
    Organic Letters
  • Probing the Role of the Mycosamine C2′-OH on the Activity of Amphotericin B
    Item type: Journal Article
    Croatt, Mitchell P.; Carreira, Erick M. (2011)
    Organic Letters
Publications 1 - 10 of 188