Highly Selective Boron‐Wittig Reaction: a Practical Method to Synthesize Trans‐Aryl Alkenes

Chemistry - A European Journal, Год журнала: 2024, Номер unknown

Опубликована: Июль 27, 2024

Olefins play an essential role in synthetic chemistry, serving not only as important synthons but also key functional groups numerous bio-active molecules. Consequently, there has been considerable interest the development of more powerful methods for olefins. While Wittig reaction stands a prominent choice olefin synthesis due to its simplicity and ready availability raw materials, limitation lies challenge controlling cis-trans selectivity, hampering broader application. In this study, novel Boron-Wittig developed utilizing gem-bis(boryl)alkanes aldehydes starting materials. This method enables creating favourable intermediates, which possess less steric hindrance, leading trans-olefins via intramolecular O-B bonds elimination. Notably, studies have validated good efficacy modifying bioactive molecules synthesizing drug with great trans-selectivity. Furthermore, mechanism was elucidated based on intermediate trapping experiments, isotope labelling studies, kinetic analyses.

Язык: Английский

Five-membered ring systems: Pyrroles and benzo analogs

Progress in heterocyclic chemistry, Год журнала: 2024, Номер unknown, С. 123 - 173

Опубликована: Янв. 1, 2024

Язык: Английский