Li Zhanjun, Zhao Lingyu, Zhang Yalin, Yan Hui, Huang Xianqiang, Shen Guodong
School of Chemistry and Chemical Engineering, School of Pharmaceutical Sciences, Liaocheng University, 1 Hunan Avenue, Liaocheng, Shandong 252000, P. R. China.
Chemistry and Chemical Engineering, Jinan University, 106 Jiwei Road, Jinan, Shandong 250022, P. R. China.
J Org Chem. 2022 Oct 7;87(19):12721-12732. doi: 10.1021/acs.joc.2c01268. Epub 2022 Sep 13.
Two concise strategies to synthesize oxazolidin-2-imines by cascade nucleophilic attack/addition cyclization reactions of ()-2-bromo-3-phenylprop-2-en-1-ols/3-phenylprop-2-yn-1-ols and diphenyl carbodiimides without a transition-metal catalyst have been developed. The reactions exhibited good substrate applicability tolerance, and a variety of substituted ()-4-(()-benzylidene)-,3-diphenyloxazolidin-2-imines were synthesized in moderate to excellent yields with good stereoselectivity. The reports also provided a convenient strategy to synthesize 3-phenylprop-2-yn-1-ols by ()-2-bromo-3-phenylprop-2-en-1-ols. The economic and practical methods provide a great advantage for potential industrial synthesis of oxazolidin-2-imines.
已经开发出两种简洁的策略，通过（）-2-溴-3-苯基丙-2-烯-1-醇/3-苯基丙-2-炔-1-醇与二苯基碳二亚胺的级联亲核进攻/加成环化反应来合成恶唑烷-2-亚胺，且无需过渡金属催化剂。这些反应表现出良好的底物适用性耐受性，以中等至优异的产率和良好的立体选择性合成了多种取代的（）-4-（（）-亚苄基）-，3-二苯基恶唑烷-2-亚胺。该报告还提供了一种通过（）-2-溴-3-苯基丙-2-烯-1-醇合成3-苯基丙-2-炔-1-醇的简便策略。这些经济实用的方法为恶唑烷-2-亚胺的潜在工业合成提供了巨大优势。
