Synthesis of <i>α</i> ‐Pentafluorosulfanylated‐ <i>β</i> <sup>2,3</sup> ‐Amino Esters
Incorporating the SF 5 group into organic molecules is a powerful strategy for pushing the boundaries of chemistry and driving progress in drug discovery. In this context,a synthetic route to backbone‐connected pentafluorosulfanyl β ‐amino esters is reported, which combine the unique physicochemical properties of the SF 5 group with those of β ‐amino acids. The approach begins with the preparation of an unprecedented library of ( E )‐ α ‐SF 5 ‐ α , β ‐unsaturated esters via aldol condensation of SF 5 acetates with aldehydes. These SF 5 ‐substituted Michael acceptors undergoes N ‐nucleophilic attack at the β ‐carbon under mild, practical conditions, affording a diverse array of α ‐SF 5 ‐ β 2,3 ‐amino esters. The reactions deliver excellent yields and high diastereoselectivity, generating syn adducts with two contiguous stereogenic centers.
Authors
- Thi Mo Nguyen (ORCID: https://orcid.org/0000-0003-3027-3483)
- Dominique Cahard (ORCID: https://orcid.org/0000-0002-8510-1315)
- Nicolas Blanchard (ORCID: https://orcid.org/0000-0002-3097-0548)
- Vincent Bizet (ORCID: https://orcid.org/0000-0002-0870-1747)
- Guilhem Colomer (ORCID: https://orcid.org/0000-0002-5541-3297)
- Oscar Maugue‐Sauze
Institutions
- Centre National de la Recherche Scientifique (FR)
- Université Paris-Saclay (FR)
- Université de Haute-Alsace (FR)
- Normandie Université (FR)
- Université de Rouen Normandie (FR)
- Institut National des Sciences Appliquées Rouen Normandie (FR)
Publication Details
- Journal
- ChemistryEurope
- Published
- 2025-10-26
- DOI
- https://doi.org/10.1002/ceur.202500255
- Citations
- 1
- Primary Topic
- Fluorine in Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 0.79
Funders
- Indian National Science Academy
- Agence Nationale de la Recherche
- Université de Strasbourg
- Centre National de la Recherche Scientifique
- Université de Rouen
- Institut Carnot Santé Animale
- European Regional Development Fund