Origami with small molecules: exploiting the C–F bond as a conformational tool

• Patrick Ryan,
• Ramsha Iftikhar and
• Luke Hunter

Beilstein J. Org. Chem. 2025, 21, 680–716, doi:10.3762/bjoc.21.54

• , fragrance chemicals, organocatalysts, and peptides. This comprehensive review summarises developments in this field during the period 2010–2024. Keywords: conformational analysis; medicinal chemistry; organofluorine chemistry; stereoselective fluorination; Introduction In the art of origami, a

Benzylic C(sp³)–H fluorination

• Alexander P. Atkins,
• Alice C. Dean and
• Alastair J. J. Lennox

Beilstein J. Org. Chem. 2024, 20, 1527–1547, doi:10.3762/bjoc.20.137

• was effective for the stereoselective fluorination of benzylic positions ortho to aldehyde substituents (Figure 9). The choice of a bulky amino, transient, directing group dictated the stereochemical outcome and promoted the C–F reductive elimination through an inner-sphere pathway. A competitive C–O

Vicinal difluorination as a C=C surrogate: an analog of piperine with enhanced solubility, photostability, and acetylcholinesterase inhibitory activity

• Yuvixza Lizarme-Salas,
• Alexandra Daryl Ariawan,
• Ranjala Ratnayake,
• Hendrik Luesch,
• Angela Finch and
• Luke Hunter

Beilstein J. Org. Chem. 2020, 16, 2663–2670, doi:10.3762/bjoc.16.216

• . Stereoselective fluorination is an emerging strategy for controlling the conformations of organic molecules. The highly polarized C–F bond tends to align in predictable ways with adjacent functional groups, due to a combination of hyperconjugative and/or dipolar interactions [18][19][20][21]. This knowledge led

Stereoselectively fluorinated N-heterocycles: a brief survey

• Xiang-Guo Hu and
• Luke Hunter

Beilstein J. Org. Chem. 2013, 9, 2696–2708, doi:10.3762/bjoc.9.306

• ]. However, with the advent of stereoselective fluorination methods [10][11] it seems clear that the subset of stereoselectively fluorinated N-heterocycles [12] offers particularly rich possibilities. We therefore felt that it would be worthwhile to examine in a brief review some of the unique features of

Single and double stereoselective fluorination of (E)-allylsilanes

• Marcin Sawicki,
• Angela Kwok,
• Matthew Tredwell and
• Véronique Gouverneur

Beilstein J. Org. Chem. 2007, 3, No. 34, doi:10.1186/1860-5397-3-34

• observation establishes the relative configuration as drawn in Scheme 2 and Scheme 3, and supports our hypothesis that the sense of stereocontrol for the fluorinations of 1e-i is in line with related nitrations reported by Panek.[28] In conclusion, the stereoselective fluorination of (E)-allylsilanes

• (±)-1a-da Fluorodesilylation (E)-allylsilanes 1e-ia Supporting Information Supporting Information File 38: Single and double stereoselective fluorination of (E)-allylsilanes. Full experimental data and procedures Acknowledgements We thank the European Community (MRTN-CT-2003-505020 and COST Action D25

Contemporary organosilicon chemistry

• Steve Marsden

Beilstein J. Org. Chem. 2007, 3, No. 4, doi:10.1186/1860-5397-3-4

• for asymmetric synthesis, and a new method for the electrochemical generation of silyl cations. Additionally, the unique nature of internet-based publishing means that the Series can grow as additional contributions are received: future papers in areas including allylation chemistry, stereoselective

• fluorination, cyclopropane chemistry and the development of silicon-containing drug candidates should be available shortly. Be sure to check back to keep abreast of the latest developments as the Series grows. Steve Marsden Guest Editor