التفاصيل البيبلوغرافية
| العنوان: |
Isothiourea-Catalysed Acylative Dynamic Kinetic Resolution of Tetra-substituted Morpholinone and Benzoxazinone Lactols |
| المؤلفون: |
Zhu, Haoxiang, Manchado, Alejandro, Farah, Abdikani Omar, McKay, Aidan, Cordes, David, Ha-Yeon Cheong, Paul, Kasten, Kevin, Smith, Andrew |
| بيانات النشر: |
American Chemical Society (ACS) |
| سنة النشر: |
2024 |
| الوصف: |
The development of methods to allow the selective acylative dynamic kinetic resolution (DKR) of tetra-substituted lactols is a recognised synthetic challenge. In this manuscript, a highly enantioselective isothiourea-catalysed acylative DKR of tetra-substituted morpholinone and benzoxazinone-derived lactols is reported. The scope and limitations of this methodology have been developed, with high enantioselectivity and good to excellent yields (up to 89%, 99:1 er) observed across a broad range of substrate derivatives incorporating substitution at N(4) and C(2), di- and spirocyclic substitution at C(5)- and C(6)-position, as well as benzannulation (>35 examples in total). The DKR process is amenable to scale-up on a 1 g laboratory scale. The factors leading to high selectivity in this DKR process have been probed through computation, with an N-C=O•••isothiouronium interaction identified as key to producing ester products in highly enantioenriched form. |
| نوع الوثيقة: |
other/unknown material |
| اللغة: |
unknown |
| DOI: |
10.26434/chemrxiv-2024-mx605 |
| الإتاحة: |
https://doi.org/10.26434/chemrxiv-2024-mx605Test
https://chemrxiv.org/engage/api-gateway/chemrxiv/assets/orp/resource/item/65b80b379138d23161fecb6c/original/isothiourea-catalysed-acylative-dynamic-kinetic-resolution-of-tetra-substituted-morpholinone-and-benzoxazinone-lactols.pdfTest |
| حقوق: |
https://creativecommons.org/licenses/by/4.0Test/ |
| رقم الانضمام: |
edsbas.24096356 |
| قاعدة البيانات: |
BASE |
