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Ruthenium-Catalyzed Diastereoselective Synthesis of Fully Substituted Pyrrolidines from Anilines and Diazo Pyruvates
Organic Letters ( IF 5.2 ) Pub Date : 2020-04-01 , DOI: 10.1021/acs.orglett.0c00846
Farrukh Sajjad 1 , Alavala Gopi Krishna Reddy 2 , Jiuwei Che 1 , Wenhao Hu 1, 2 , Dong Xing 1
Affiliation  

An unprecedented synthesis of polysubstituted pyrrolidines from anilines and diazo pyruvates by ruthenium catalysis under mild reaction conditions is reported. An enol intermediate derived from the N–H insertion of aniline toward the ruthenium carbene species as well as an imine ester intermediate generated by SET-mediated oxidation of enol were proposed as the key intermediates. This strategy provides various pyrrolidines containing four contiguous stereocenters in good efficiency with high diastereoselectivities.

中文翻译:

钌催化苯胺和重氮丙酮酸酯完全取代的吡咯烷酮的非对映选择性合成

据报道,在温和的反应条件下,钌催化空前地由苯胺和重氮丙酮酸酯合成多取代的吡咯烷。作为关键中间体,有人提出了由苯胺向钌卡宾物种的N–H插入所衍生的烯醇中间体,以及由SET介导的烯醇氧化生成的亚胺酯中间体。该策略以高效率和高非对映选择性提供了包含四个连续立体中心的各种吡咯烷。
更新日期:2020-04-24
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