Enantioselective Synthesis of Pyroglutamic Acid Esters from Glycinate via Carbonyl Catalysis
| العنوان: | Enantioselective Synthesis of Pyroglutamic Acid Esters from Glycinate via Carbonyl Catalysis |
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| المؤلفون: | Guanshui Song, Qinghai Zhou, Guoqing Zhao, Yongchang Song, Baoguo Zhao, Jiguo Ma, Kuiling Ding |
| المصدر: | Angewandte Chemie. 133:10682-10686 |
| بيانات النشر: | Wiley, 2021. |
| سنة النشر: | 2021 |
| مصطلحات موضوعية: | 010405 organic chemistry, Chemistry, Absolute configuration, Enantioselective synthesis, Diastereomer, General Chemistry, General Medicine, 010402 general chemistry, 01 natural sciences, Medicinal chemistry, Catalysis, 0104 chemical sciences, chemistry.chemical_compound, Electrophile, Organic synthesis, Pyroglutamic acid, Barton decarboxylation |
| الوصف: | Direct a-functionalization of NH 2 -free glycinates with relatively weak electrophiles such as α,β-unsaturated esters still remains a big challenge in organic synthesis. With chiral pyridoxal 5d as a carbonyl catalyst, direct asymmetric conjugated addition at the α-C of glycinate 1a with α,β-unsaturated esters 2 has been successfully realized, to produce various chiral p yroglutamic acid esters 4 in 14~96% yields with 81~97% ee's after in situ lactamization. The trans - and cis -diastereomers can be obtained at the same time by chromatography and both of them can be easily converted into chiral 4-substituted pyrrolidin-2-ones such as Alzheimer's drug Rolipram ( 11 ) with the same absolute configuration via tert -butyl group removal and subsequent Barton decarboxylation. |
| تدمد: | 1521-3757 0044-8249 |
| URL الوصول: | https://explore.openaire.eu/search/publication?articleId=doi_dedup___::0d2e6ee2bbcb5864db6e67f3ca4c110e https://doi.org/10.1002/ange.202017306 |
| حقوق: | CLOSED |
| رقم الأكسشن: | edsair.doi.dedup.....0d2e6ee2bbcb5864db6e67f3ca4c110e |
| قاعدة البيانات: | OpenAIRE |
| تدمد: | 15213757 00448249 |
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