Supramolecular Science and Engineering Institute, University of Strasbourg, CNRS, 67000, Strasbourg, France.
Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, MA 02467, USA.
Angew Chem Int Ed Engl. 2022 Nov 14;61(46):e202208742. doi: 10.1002/anie.202208742. Epub 2022 Oct 6.
Stereochemically defined organofluorine compounds are vital to drug discovery and many applicable catalytic strategies have been introduced for accessing these entities stereoselectively. One approach entails incorporation of a fluorine atom (C-F bond formation) or an organofluorine moiety (e.g., CF or CF H), and another exploits commercially available compounds with one or more fluorine atoms. Here, we present the state-of-the-art regarding the use of alkenyl and allylic fluorides in preparation of stereochemically defined fluoro-organic molecules. Allylic and alkenyl fluorides may be purchased or generated from a commercially available acid, carboxylate salt, ester, aldehyde hydrate, or ketone bearing several fluorine atoms next to a carbonyl group. We underscore the untapped potential of purchasable organofluorine compounds, many allylic and alkenyl fluorides, as launching points for development of stereoselective processes that are of value to therapeutic science.
立体化学定义明确的有机氟化合物对于药物发现至关重要，已经引入了许多适用的催化策略来立体选择性地获得这些化合物。一种方法涉及引入一个氟原子（C-F 键形成）或一个有机氟部分（例如 CF 或 CFH），另一种方法则利用具有一个或多个氟原子的商业上可获得的化合物。在这里，我们介绍了在制备立体化学定义明确的氟有机分子中使用烯基和烯丙基氟化物的最新进展。烯丙基和烯基氟化物可以从市售的酸、羧酸盐、酯、醛水合物或酮购买，也可以从其生成，这些化合物在羰基的旁边带有几个氟原子。我们强调了可购买的有机氟化合物的未开发潜力，许多烯丙基和烯基氟化物可作为开发对治疗科学有价值的立体选择性过程的起点。
