دورية أكاديمية

Discrimination of the Enantiotopic Faces of Structurally Unbiased Carbenium Ions Employing a Cyclohexadiene‐Based Chiral Hydride Source

التفاصيل البيبلوغرافية
العنوان: Discrimination of the Enantiotopic Faces of Structurally Unbiased Carbenium Ions Employing a Cyclohexadiene‐Based Chiral Hydride Source
المؤلفون: Wolff, Benedikt, Qu, Zheng‐Wang, Grimme, Stefan, Oestreich, Martin
المساهمون: Deutsche Forschungsgemeinschaft, Einstein Stiftung Berlin, Technische Universität Berlin
المصدر: Angewandte Chemie International Edition ; volume 62, issue 29 ; ISSN 1433-7851 1521-3773
بيانات النشر: Wiley
سنة النشر: 2023
المجموعة: Wiley Online Library (Open Access Articles via Crossref)
الوصف: An enantioselective reduction of simple carbenium ions with cyclohexadienes containing a hydridic C−H bond at an asymmetrically substituted carbon atom is disclosed. The net reaction is a transfer hydrogenation of alkenes (styrenes) only employing chiral cyclohexadienes as dihydrogen surrogates. The trityl cation is used to initiate a Brønsted acid‐promoted process, in which a delicate intermolecular capture of a carbenium‐ion intermediate by the aforementioned chiral hydride source is enantioselectivity determining. Exclusively non‐covalent interactions are rendering one of the transition states energetically more favored, giving the reduction products in good enantiomeric ratios. The computed reaction mechanism supports the present findings as well as previous results obtained from studies on other transfer‐hydrogenation methods involving the cyclohexadiene platform.
نوع الوثيقة: article in journal/newspaper
اللغة: English
DOI: 10.1002/anie.202305295
الإتاحة: https://doi.org/10.1002/anie.202305295Test
حقوق: http://creativecommons.org/licenses/by/4.0Test/
رقم الانضمام: edsbas.3A1FFF14
قاعدة البيانات: BASE