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Catalytic Asymmetric Chemodivergent C2 Alkylation and [3 + 2]-Cycloaddition of 3-Methylindoles with Aziridines
ACS Catalysis ( IF 11.3 ) Pub Date : 2018-10-03 00:00:00 , DOI: 10.1021/acscatal.8b02880 Yali Xu 1 , Fenzhen Chang 1 , Weidi Cao 1 , Xiaohua Liu 1 , Xiaoming Feng 1
ACS Catalysis ( IF 11.3 ) Pub Date : 2018-10-03 00:00:00 , DOI: 10.1021/acscatal.8b02880 Yali Xu 1 , Fenzhen Chang 1 , Weidi Cao 1 , Xiaohua Liu 1 , Xiaoming Feng 1
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Highly enantioselective C2 alkylation and inverse-electron-demand [3 + 2]-cycloaddition of 3-methylindoles with 2,2′-diester aziridine were accomplished. The chemodivergent synthesis provided an access to two kinds of chiral indole derivatives in good yields and stereoselectivities in the presence of the chiral N,N′-dioxide/Tm(OTf)3 or N,N′-dioxide/Ho(OTf)3 complexes. An eight-coordinated mode of N,N′-dioxide/Tm(OTf)3 complex was confirmed by X-ray crystal diffraction to interpret the roles of additives H2O and 1,4-dioxane. In addition, the control experiments indicated that the substituent of the indole nitrogen atom determined the conversion patterns in the divergent reactions.
中文翻译：
催化不对称化学发散性C2烷基化和3-甲基吲哚与氮丙啶的[3 + 2]-环加成反应
实现了高对映选择性的C2烷基化和3-甲基吲哚与2,2'-二酯氮丙啶的电子反需求[3 + 2]-环加成反应。在存在手性N，N'-二氧化物/ Tm（OTf）3或N，N'-二氧化物/ Ho（OTf）3配合物的情况下，化学发散合成提供了良好收率和立体选择性的两种手性吲哚衍生物的途径。。的八协调模式Ñ，ñ '二氧化物/ TM（OTF）3复合物通过X射线晶体衍射证实解释添加剂的作用ħ 2O和1，4-二恶烷。另外，对照实验表明，吲哚氮原子的取代基决定了发散反应中的转化方式。
更新日期：2018-10-03
中文翻译：
催化不对称化学发散性C2烷基化和3-甲基吲哚与氮丙啶的[3 + 2]-环加成反应
实现了高对映选择性的C2烷基化和3-甲基吲哚与2,2'-二酯氮丙啶的电子反需求[3 + 2]-环加成反应。在存在手性N，N'-二氧化物/ Tm（OTf）3或N，N'-二氧化物/ Ho（OTf）3配合物的情况下，化学发散合成提供了良好收率和立体选择性的两种手性吲哚衍生物的途径。。的八协调模式Ñ，ñ '二氧化物/ TM（OTF）3复合物通过X射线晶体衍射证实解释添加剂的作用ħ 2O和1，4-二恶烷。另外，对照实验表明，吲哚氮原子的取代基决定了发散反应中的转化方式。
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